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73895-87-1

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73895-87-1 Usage

Uses

Ethyl (4-Amino-2-nitrophenyl)carbamate is an impurity of Retigabine (R189050), an anticonvulsant drug.

Check Digit Verification of cas no

The CAS Registry Mumber 73895-87-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,3,8,9 and 5 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 73895-87:
(7*7)+(6*3)+(5*8)+(4*9)+(3*5)+(2*8)+(1*7)=181
181 % 10 = 1
So 73895-87-1 is a valid CAS Registry Number.

73895-87-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name Ethyl (4-amino-2-nitrophenyl)carbamate

1.2 Other means of identification

Product number -
Other names ethyl 4-amino-2-nitrophenyl carbamate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:73895-87-1 SDS

73895-87-1Synthetic route

2-ethoxycarbonylamino-5-phthalimidonitrobenzene
150812-24-1

2-ethoxycarbonylamino-5-phthalimidonitrobenzene

5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

Conditions
ConditionsYield
With methylamine In water; isopropyl alcohol at 60 - 65℃; for 2h; Concentration; Reagent/catalyst; Solvent; Temperature; Time;97.2%
With hydrazine In 1,2-dimethoxyethane for 1.66667h; Heating / reflux;90%
With hydrazine hydrate In 1,2-dimethoxyethane
N-(4-aminophenyl)carbamic acid ethyl ester
57399-97-0

N-(4-aminophenyl)carbamic acid ethyl ester

5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

Conditions
ConditionsYield
With sulfuric acid; nitric acid In water at -5 - 0℃; for 0.5h; Inert atmosphere;60%
Stage #1: N-(4-aminophenyl)carbamic acid ethyl ester With sulfuric acid In water at -5℃;
Stage #2: With nitric acid In water at 0℃; for 0.5h; Inert atmosphere;
60%
Multi-step reaction with 3 steps
1: N,N-dimethyl-formamide / 2.5 h / 20 - 95 °C / Inert atmosphere
2: nitric acid / acetic acid / 20 - 105 °C / Inert atmosphere
3: methylamine / isopropyl alcohol; water / 2 h / 60 - 65 °C
View Scheme
1-ethoxycarbonylamino-4-phthalimidobenzene
721943-05-1

1-ethoxycarbonylamino-4-phthalimidobenzene

5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: nitric acid / acetic acid / 20 - 105 °C / Inert atmosphere
2: methylamine / isopropyl alcohol; water / 2 h / 60 - 65 °C
View Scheme
ethyl 4-nitrophenylcarbamate
2621-73-0

ethyl 4-nitrophenylcarbamate

5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ammonium formate; 5%-palladium/activated carbon / tetrahydrofuran; water / 24 h / 50 °C / Inert atmosphere
2: sulfuric acid; nitric acid / water / 0.5 h / -5 - 0 °C / Inert atmosphere
View Scheme
5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

2-ethoxycarbonylamino-5-(4-fluorobenzylideneamino)nitrobenzene
1314406-56-8

2-ethoxycarbonylamino-5-(4-fluorobenzylideneamino)nitrobenzene

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 4h; Reflux;100%
In ethanol at 20 - 65℃; Solvent; Temperature;97.9%
5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

3-Fluorobenzaldehyde
456-48-4

3-Fluorobenzaldehyde

C16H16FN3O4

C16H16FN3O4

Conditions
ConditionsYield
Stage #1: 5-amino-2-ethoxycarbonylaminonitrobenzene; 3-Fluorobenzaldehyde With toluene-4-sulfonic acid In toluene for 4h; Reflux;
Stage #2: With methanol; sodium tetrahydroborate In ethyl acetate at 10℃; for 4h;
88.6%
5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

2-Fluorobenzaldehyde
446-52-6

2-Fluorobenzaldehyde

C16H16FN3O4

C16H16FN3O4

Conditions
ConditionsYield
Stage #1: 5-amino-2-ethoxycarbonylaminonitrobenzene; 2-Fluorobenzaldehyde With toluene-4-sulfonic acid In toluene for 4h; Reflux;
Stage #2: With methanol; sodium tetrahydroborate In ethyl acetate at 10℃; for 4h;
87%
5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

2-ethoxycarbonylamino-5-(4-fluorobenzylamino)nitrobenzene
150812-23-0

2-ethoxycarbonylamino-5-(4-fluorobenzylamino)nitrobenzene

Conditions
ConditionsYield
With sodium tetrahydroborate In water; isopropyl alcohol at 20℃; Solvent; Temperature; Time;81.7%
Stage #1: 5-amino-2-ethoxycarbonylaminonitrobenzene With sodium tetrahydroborate; acetic acid In tetrahydrofuran at 35℃;
Stage #2: 4-fluorobenzaldehyde In tetrahydrofuran at 35℃; for 1h;
5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

4-(4-chloro-benzenesulfonyl)-3-methyl-thiophene-2-carbaldehyde
721943-14-2

4-(4-chloro-benzenesulfonyl)-3-methyl-thiophene-2-carbaldehyde

C21H18ClN3O6S2
721943-40-4

C21H18ClN3O6S2

Conditions
ConditionsYield
In ethanol for 20h; Heating / reflux;61%
5-Chloro-2-thiophenecarboxaldehyde
7283-96-7

5-Chloro-2-thiophenecarboxaldehyde

5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

(2-amino-4-((5-chloro-thiophen-2-ylmethyl)-amino)-phenyl)-carbamic acid ethyl ester

(2-amino-4-((5-chloro-thiophen-2-ylmethyl)-amino)-phenyl)-carbamic acid ethyl ester

Conditions
ConditionsYield
Stage #1: 5-Chloro-2-thiophenecarboxaldehyde; 5-amino-2-ethoxycarbonylaminonitrobenzene With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 40℃; for 3.5h; Ultrasonic bath;
Stage #2: With hydrogenchloride; iron In ethanol; water for 0.166667h;
56%
5-methylthiophene-2-carboxaldehyde
13679-70-4

5-methylthiophene-2-carboxaldehyde

5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

C15H15N3O4S

C15H15N3O4S

Conditions
ConditionsYield
Amberlite IRC-84 In o-xylene for 5h; Heating / reflux;
5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

5-fluorobenzofuran-3-carbaldehyde
721943-19-7

5-fluorobenzofuran-3-carbaldehyde

C18H14FN3O5

C18H14FN3O5

Conditions
ConditionsYield
Amberlite IRC-84 In o-xylene for 5h; Heating / reflux;
5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

2-ethoxycarbonylamino-5-(4-fluorobenzylamino)nitrobenzene
150812-23-0

2-ethoxycarbonylamino-5-(4-fluorobenzylamino)nitrobenzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ethanol / 20 - 65 °C
2: sodium tetrahydroborate / isopropyl alcohol; water / 0 - 30 °C
View Scheme
Multi-step reaction with 2 steps
1: toluene-4-sulfonic acid / toluene / 4 h / Reflux
2: sodium tetrahydroborate; methanol / ethyl acetate / 4 h / 10 °C
View Scheme
5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

Retigabine
150812-12-7

Retigabine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / isopropyl alcohol; water / 20 °C
2: hydrogen; palladium 10% on activated carbon; ammonia / methanol / 25 - 30 °C / 2250.23 - 3000.3 Torr / Inert atmosphere; Autoclave
View Scheme
Multi-step reaction with 2 steps
1: ethanol / 20 - 65 °C
2: hydrogen; palladium 10% on activated carbon; triethylamine / methanol / 25 - 30 °C / 2250.23 - 3000.3 Torr / Inert atmosphere; Autoclave
View Scheme
Multi-step reaction with 3 steps
1: ethanol / 20 - 65 °C
2: sodium tetrahydroborate / isopropyl alcohol; water / 0 - 30 °C
3: hydrogen; palladium 10% on activated carbon; ammonia / methanol / 25 - 30 °C / 2250.23 - 3000.3 Torr / Inert atmosphere; Autoclave
View Scheme
Multi-step reaction with 2 steps
1.1: acetic acid; sodium tetrahydroborate / tetrahydrofuran / 35 °C
1.2: 1 h / 35 °C
2.1: hydrogenchloride; iron / water; ethanol / 1 h / 25 °C
View Scheme
Multi-step reaction with 3 steps
1: toluene-4-sulfonic acid / toluene / 4 h / Reflux
2: sodium tetrahydroborate; methanol / ethyl acetate / 4 h / 10 °C
3: hydrogen / ethyl acetate / 15 h / 55 - 60 °C / 8250.83 Torr
View Scheme
5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

retigabine dihydrochloride

retigabine dihydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium tetrahydroborate / isopropyl alcohol; water / 20 °C
2: hydrogen; palladium 10% on activated carbon; ammonia / methanol / 25 - 30 °C / 2250.23 - 3000.3 Torr / Inert atmosphere; Autoclave
3: hydrogenchloride / methanol / 2 h / 25 - 30 °C
View Scheme
Multi-step reaction with 3 steps
1: ethanol / 20 - 65 °C
2: hydrogen; palladium 10% on activated carbon; triethylamine / methanol / 25 - 30 °C / 2250.23 - 3000.3 Torr / Inert atmosphere; Autoclave
3: hydrogenchloride / methanol / 2 h / 25 - 30 °C
View Scheme
Multi-step reaction with 4 steps
1: ethanol / 20 - 65 °C
2: sodium tetrahydroborate / isopropyl alcohol; water / 0 - 30 °C
3: hydrogen; palladium 10% on activated carbon; ammonia / methanol / 25 - 30 °C / 2250.23 - 3000.3 Torr / Inert atmosphere; Autoclave
4: hydrogenchloride / methanol / 2 h / 25 - 30 °C
View Scheme
5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

Retigabine
150812-12-7

Retigabine

Conditions
ConditionsYield
Stage #1: 5-amino-2-ethoxycarbonylaminonitrobenzene; 4-fluorobenzaldehyde With sodium tetrahydroborate; acetic acid In tetrahydrofuran at 25 - 35℃;
Stage #2: With hydrogenchloride; iron In ethanol; water at 25℃; for 1h;
5-amino-2-ethoxycarbonylaminonitrobenzene
73895-87-1

5-amino-2-ethoxycarbonylaminonitrobenzene

2-Fluorobenzaldehyde
446-52-6

2-Fluorobenzaldehyde

C16H18FN3O2

C16H18FN3O2

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: toluene-4-sulfonic acid / toluene / 4 h / Reflux
1.2: 4 h / 10 °C
2.1: hydrogen / ethyl acetate / 15 h / 55 - 60 °C / 8250.83 Torr
View Scheme

73895-87-1Relevant articles and documents

Process for the preparation of an anticonvulsant compound

-

, (2014/05/24)

The invention provides a novel method for the preparation of intermediates useful in a process designed to obtain known 1,2,4-triaminobenzene compounds, and in particular a specific compound thereof having known anticonvulsant activity. Unlike known methods, the novel method does not require advance protection of the amino groups present on the substrate.

PROCESS FOR THE PREPARATION OF RETIGABINE OF THE FORMULA I AND PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF

-

, (2013/03/26)

The invention relates to process for the preparation of 2-amino-4-(4- fluorobenzylamino)-l-ethoxycarbonylaminobenzene generically known as Retigabine of the formula (I) and its pharmaceutically acceptable salts e.g. Formula IA, particularly to the modification over the prior art processes-I and II disclosed therein in US5384330. The modifications are depicted in the scheme I and scheme II respectively. Disclosed herein are also the novel processes for the preparation of intermediates of formulae M, N and O of the process-I and of formulae R, S, T of process-II, those are used for preparation of Retigabine of the formula I and its pharmaceutically acceptable salts thereof.

Pharmaceutically active 1,2,4-triamino-benzene derivatives, processes for their preparation and pharmaceutical compositions containing them

-

, (2008/06/13)

Pharmacologically active 1,2,4-triaminobenzene derivatives of the General Formula I: STR1 where the symbols R1' R2' R3' R4' R5' Ar and Alk have the following meanings: where the symbols R1, R2, R3, R4, R5, Ar and Alk have the following meanings: R1 : hydrogen, C1 -C6 -alkyl, C2 -C6 -alkanoyl or the radical Ar; R2 : hydrogen or C1 -C6 -alkyl; R3 : C1 -C6 -alkoxy, NH2, C1 -C6 -alkylamino, C1 -C6 -dialkylamino, amino substituted by the radical Ar, C1 -C6 -alkyl, C2 -C6 -alkenyl, C2 -C6 -alkynyl, the radical Ar or the radical ArO--; R4 : hydrogen, C1 -C6 -alkyl or the radical Ar; R5 : hydrogen or C1 -C6 -alkyl or the radical Ar; Alk: a straight or branched alkylene group containing 1-9 carbon atoms, which can also be substituted by the radical Ar.

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