(Z)-S-Benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-((trityloxy)imino)ethanethioate

Base Information

• Chemical Name: (Z)-S-Benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-((trityloxy)imino)ethanethioate
• CAS No.: 143183-03-3
• Molecular Formula: C31H22N4O2S3
• Molecular Weight: 578.739
• European Community (EC) Number: 700-114-7
• Mol file: 143183-03-3.mol

Synonyms:143183-03-3;(Z)-S-Benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-((trityloxy)imino)ethanethioate;S-(1,3-benzothiazol-2-yl) (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-trityloxyiminoethanethioate;Benzothiazol-2-yl)-(Z)-2-trityloxyimino -2-(2-Aminothiazole-4-yl-)-Thioacetate;EC 700-114-7;SCHEMBL13926071;AKOS015963050;AC-5574;S-1,3-benzothiazol-2-yl (2Z)-(2-amino-1,3-thiazol-4-yl)((trityloxy)imino)ethanethioate;AS-74062;A808033;J-502664;(Z)-O-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-((trityloxy)imino)ethanethioate;(Z)-S-Benzo[d]thiazol-2-yl2-(2-aminothiazol-4-yl)-2-((trityloxy)imino)ethanethioate;(2Z)-2-(2-amino-1,3-thiazol-4-yl)-1-(1,3-benzothiazol-2-ylsulfanyl)-2-[(triphenylmethoxy)imino]ethan-1-one

Chemical Property of (Z)-S-Benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-((trityloxy)imino)ethanethioate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.721
• Boiling Point: 767.438 °C at 760 mmHg
• PKA: 0.90±0.10(Predicted)
• Flash Point: 417.932 °C
• PSA: 171.19000
• Density: 1.367 g/cm³
• LogP: 8.03540
• XLogP3: 8.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 9
• Exact Mass: 578.09048948
• Heavy Atom Count: 40
• Complexity: 827

Purity/Quality:

99% ^*data from raw suppliers

(Z)-S-Benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-((trityloxy)imino)ethanethioate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)ON=C(C4=CSC(=N4)N)C(=O)SC5=NC6=CC=CC=C6S5
• Isomeric SMILES: C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)O/N=C(/C4=CSC(=N4)N)\C(=O)SC5=NC6=CC=CC=C6S5

Technology Process of (Z)-S-Benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-((trityloxy)imino)ethanethioate

There total 5 articles about (Z)-S-Benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-((trityloxy)imino)ethanethioate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 65.0%

di(benzothiazol-2-yl)disulfide (120-78-5) + (Z)-2-(2-aminothiazol-4-yl)-2-(triphenylmethoxyimino)acetic acid (128438-01-7) → S-(2-benzothiazolyl) 2-(2-aminothiazol-4-yl)-2(Z)-trityloxyiminothioacetate (143183-03-3)

Guidance literature:

With tributyl-amine; triethyl phosphite; In acetonitrile; at 5 ℃; for 15h;

DOI:10.7164/antibiotics.53.1053

Reference yield:

trityl chloride (76-83-5) → S-(2-benzothiazolyl) 2-(2-aminothiazol-4-yl)-2(Z)-trityloxyiminothioacetate (143183-03-3)

Guidance literature:

Multi-step reaction with 2 steps

2: 1.) Ph₃P / 1.) CH₂Cl₂, r.t., 40 min, 2.) r.t., 1.5 h

With triphenylphosphine;

DOI:10.1002/jlac.199619961107

Reference yield:

(Z)-ethyl 2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetate (64485-82-1) → S-(2-benzothiazolyl) 2-(2-aminothiazol-4-yl)-2(Z)-trityloxyiminothioacetate (143183-03-3)

Guidance literature:

Multi-step reaction with 2 steps

2: 1.) Ph₃P / 1.) CH₂Cl₂, r.t., 40 min, 2.) r.t., 1.5 h

With triphenylphosphine;

DOI:10.1002/jlac.199619961107

upstream raw materials:

di(benzothiazol-2-yl)disulfide

(Z)-2-(2-aminothiazol-4-yl)-2-(triphenylmethoxyimino)acetic acid

trityl chloride

(Z)-ethyl 2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetate

Downstream raw materials:

N,N'-dicyclohexylethane-1,2-diamine salt of 7β-[2-(2-amino-4-thiazolyl)-2-((Z)-hydroxyimino)acetamido]-3-vinyl-3-cephem-4-carboxylic acid

(6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-trityloxyimino]-acetylamino}-3-methoxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (S)-1-(2,2-dimethyl-propionyloxy)-ethyl ester

cefdinir

Refernces

• 1、 Defossa, Elisabeth,Fischer, Gerd,Gerlach, Uwe,Hoerlein, Rolf,Isert, Dieter,Krass, Norbert,Lattrell, Rudolf,Stache, Ulrich,Wollmann, Theo. "Synthesis of HR 916 K: An efficient route to the pure diastereomers of the 1-(pivaloyloxy)ethyl esters of cephalosporins". . p. 1743 - 1749. Retrieved 2007/10/03.