40279-09-2

Basic information

• Product Name: 1H-Imidazole, 2-(methylthio)-1-phenyl-
• CAS NO: 40279-09-2
• Molecular Formula: C10H10N2S
• Molecular Weight: 190.269
• Mol File: 40279-09-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1H-Imidazole, 2-(methylthio)-1-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Imidazole, 2-(methylthio)-1-phenyl-(40279-09-2)
• EPA Substance Registry System: 1H-Imidazole, 2-(methylthio)-1-phenyl-(40279-09-2)

Safety Data

• Hazardous Substances Data: 40279-09-2(Hazardous Substances Data)

Upstream product

• 103-72-0 phenyl isothiocyanate 
• 17452-09-4 1-phenyl-2-mercaptoimidazol 
• 74-88-4 methyl iodide 
• 18805-23-7 N-(Phenyl)imidodithiokohlensaeure-S,S'-dimethylester 
• 645-36-3 2,2-diethoxy-ethanamine 
• 7164-98-9 1-phenylimidazole 
• 624-92-0 Dimethyldisulphide 

Downstream Products

• 18192-01-3 2-methylsulphonyl-5-nitro-1-phenylimidazole 
• 85694-81-1 3-Methanesulfonyl-5'-nitro-1'-phenyl-4,5-dihydro-3H,1'H-[1,2']biimidazolyl-2-one 
• 154475-21-5 2-methylsulfonyl-1-phenylimidazole 
• 18192-00-2 2-methylmercapto-5-nitro-1-phenylimidazole 

Relevant articles and documents

Transfer of Alkoxycarbonyl from Alkyl Imidazolium-2-carboxylates to Benzyl Alcohol, a Cyclohexanone Enamine and Diethylamine

Alkylimidazole-2-carboxylates may be alkylated with methyl triflate to give the corresponding N-methylimidazolium salts.These salts react with benzyl alcohol in the presence of 1,4-diazabicyclooctane, with 1-(pyrrolidin-1-yl)cyclohexene and with diethylamine to give benzyl alkyl carbonates, an enamino ester and a urethane respectively; in one case a tetrahedral intermediate is observed.The corresponding phenyl ester was consumed without attack by benzyl alcohol at the carbonyl group.A 2-cyanoimidazolium salt underwent similar ill-defined consumption whereas a 2-dimethylaminocarbonyl derivative remained unchanged. 2-Methylsulfonylimidazolium salts suffered attack by benzyl alcohol at the ring C-2.

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.