56302-13-7

Basic information

• Product Name: Satranidazole
• Synonyms: Satranidazole;1-(1-Methyl-5-nitro-1H-imidazol-2-yl)-3-(methylsulfonyl)-2-imidazolidinone;CG-10213Go;Go-10213;Satranidazole, 1-(1-methyl-5-nitro-1H-imidazol-2-yl)-3-(methylsulfonyl)imidazolidin-2-one;Satranidazole iMpurity
• CAS NO: 56302-13-7
• Molecular Formula: C₈H₁₁N₅O₅S
• Molecular Weight: 289.30
• Mol File: 56302-13-7.mol
• Article Data: 2

Chemical Properties

• Melting Point: 185°C
• Boiling Point: 505.2°Cat760mmHg
• Flash Point: 259.3°C
• Appearance: /
• Density: 1.5943 (rough estimate)
• Vapor Pressure: 2.48E-10mmHg at 25°C
• Refractive Index: 1.6460 (estimate)
• PKA: 2.49±0.25(Predicted)
• CAS DataBase Reference: Satranidazole(CAS DataBase Reference)
• NIST Chemistry Reference: Satranidazole(56302-13-7)
• EPA Substance Registry System: Satranidazole(56302-13-7)

Safety Data

• Hazardous Substances Data: 56302-13-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H11N5O5S/c1-10-6(13(15)16)5-9-7(10)11-3-4-12(8(11)14)19(2,17)18/h5H,3-4H2,1-2H3

Synthetic route

1-(methylsulphonyl)-2-oxo-2,3,4,5-tetrahydroimidazole (41730-79-4) + 1-methyl-2-methylsulphonyl-5-nitro-imidazole (1615-53-8) → 1 (1 methyl 5 nitroimidazol 2 yl) 3 (methylsulfonyl)imidazolidin 2 one (56302-13-7)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 25℃; for 5h;	80%

1-methylsulphonyl-3-(1-methyl-2-imidazolyl)-2-imidazolidinone (85695-00-7) → 1 (1 methyl 5 nitroimidazol 2 yl) 3 (methylsulfonyl)imidazolidin 2 one (56302-13-7)

Conditions	Yield
With sulfuric acid; nitric acid at 120℃; for 1.5h;	15 mg

2-chloro-1-methyl-5-nitroimidazole (86072-07-3) + 1-(methylsulphonyl)-2-oxo-2,3,4,5-tetrahydroimidazole (41730-79-4) → 1 (1 methyl 5 nitroimidazol 2 yl) 3 (methylsulfonyl)imidazolidin 2 one (56302-13-7)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide 1.) 30 min, room temperature, 2.) a) 1 h, room temperture, b) 3 h, 55 deg C, c) room temperature;	0.9 g

1-(1-methyl-imidazolyl)-2-imidazolidinone hydrochloride → 1 (1 methyl 5 nitroimidazol 2 yl) 3 (methylsulfonyl)imidazolidin 2 one (56302-13-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.1 g / NaH / dimethylformamide; dioxane / 1) 0-5 deg C, 1 h, 2) RT, 12 h 2: 15 mg / conc. H2SO4, HNO3 (d 1.42) / 1.5 h / 120 °C View Scheme

triethyloxonium fluoroborate (368-39-8) + 1 (1 methyl 5 nitroimidazol 2 yl) 3 (methylsulfonyl)imidazolidin 2 one (56302-13-7) → 3-ethyl-1-methyl-5-nitro-2-(3-methylsulphonyl-2-oxotetrahydroimidazolyl-1-) imidazolium fluoroborate

Conditions	Yield
In chloroform for 72h; Ambient temperature;	0.85 g

1 (1 methyl 5 nitroimidazol 2 yl) 3 (methylsulfonyl)imidazolidin 2 one (56302-13-7) → 5'-Amino-3-methanesulfonyl-1'-methyl-4,5-dihydro-3H,1'H-[1,2']biimidazolyl-2-one

Conditions	Yield
With hydrogen; sodium sulfate; nickel In ethyl acetate; N,N-dimethyl-formamide at 45℃;
With hydrogenchloride; zinc

1 (1 methyl 5 nitroimidazol 2 yl) 3 (methylsulfonyl)imidazolidin 2 one (56302-13-7) → 2-(2-methanesulphonamidoethylamino)-1-methyl-5-nitroimidazole (134307-48-5)

Conditions	Yield
With hydroxide	0.1 g

1 (1 methyl 5 nitroimidazol 2 yl) 3 (methylsulfonyl)imidazolidin 2 one (56302-13-7) → 1-methanesulphonyl-3-(5-nitro-1H-imidazol-2-yl)-2-imidazolidinone (85695-08-5) + 1-methanesulphonyl-3-(1-methyl-4-nitro-1H-imidazol-2-yl)-2-imidazolidinone (56302-24-0)

Conditions	Yield
With potassium iodide In N,N-dimethyl-formamide for 20h; Heating;	A 1.8 g B 2.1 g
With potassium iodide In N,N-dimethyl-formamide Heating;

Upstream product

• 41730-79-4 1-(methylsulphonyl)-2-oxo-2,3,4,5-tetrahydroimidazole 
• 1615-53-8 1-methyl-2-methylsulphonyl-5-nitro-imidazole 
• 86072-07-3 2-chloro-1-methyl-5-nitroimidazole 
• 85695-00-7 1-methylsulphonyl-3-(1-methyl-2-imidazolyl)-2-imidazolidinone 

Relevant articles and documents

Nitroimidazoles: Part IV - 1-Sulphonyl(carbamoyl/thiocarbamoyl)-3-(1-methyl-5-nitroimidazol-2-yl)-2-imidazolidinones

Sulphone (5) is condensed with sodium salts of a variety of 1-suplphonyl (7), 1-thiocarbamoyl (9) and 1-carbonyl (10)-2-imidazolidinones to give 3-(2-imidazolyl)imidazolidinones (12), (13) and (14) respectively, out of which 1-methylsulphonyl-3-(1-methyl-5-nitro-imidazol-2-yl)-2-imidazolidinone (12a) is undergoing clinical trials as an antiamoebic-antitrichomonal agent. 15 and 16 are analougous imidazolidinones, while 17 and 18 are benzimidazolone derivatives.The reaction of 5 with the sodium salt of 2-imidazolidinone gives rise to the mono and bis-condensation products 21 and 22 respectively.Several other minor byproducts, 23-27 have been identified. 23, 26 and 27 arise from 21. 24, a transformation product of 5 leads to the ether 25 by a displacement reaction.A second synthesis of 12a involves the nitration of imidazolylimidazolidinone (30) in the terminal step, with 30 becoming available from 1-methyl-2-aminoimidazole (28) and chloroethyl isocyanate, and subsequent reaction of resultant 29 with methanesulphonyl chloride.The higher ring homologue, 33 of 12a is synthesised in poor yield from 5 and 1-methylsulphonylhexahydropyrimidinone.Treatment of 12a and 13a with KI in DMF leads to the isomeric 4-nitro derivatives 38a, b and desmethyl derivates 37a, b.Treatment of 12a with triethyloxonium fluoroborate affords the quaternary isothiourea (35) which is hydrolysed to 36.Treatment of 12a and 13a with aqeous alkali leads to cleavage of imidazolidinone ring to form the ethylenediamines 31a and b.Position isomers 41 and 43 of 12a are respetcively obtained by the reaction of 1-methyl-4-nitro-5-chloro-(40)-, and 1-methyl-5-nitro-4-chloro-(42)-imidazoles with 1-methylsulphonyl-ethylene urea.Treatment of the last compound with various reactive halides, e.g. 2-chlorobenzothiazole, yields several analogues 44a-i of 12a while niridazole (45) and methylsulphonyl chloride affords nitrothiazole analogue 46.