249608-72-8

Basic information

• Product Name: (2-isothiocyanatophenyl)(1H-pyrrol-2-yl)methanone
• Synonyms: (2-isothiocyanatophenyl)(1H-pyrrol-2-yl)methanone
• CAS NO: 249608-72-8
• Molecular Weight: 228.274
• Mol File: 249608-72-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2-isothiocyanatophenyl)(1H-pyrrol-2-yl)methanone(CAS DataBase Reference)
• NIST Chemistry Reference: (2-isothiocyanatophenyl)(1H-pyrrol-2-yl)methanone(249608-72-8)
• EPA Substance Registry System: (2-isothiocyanatophenyl)(1H-pyrrol-2-yl)methanone(249608-72-8)

Safety Data

• Hazardous Substances Data: 249608-72-8(Hazardous Substances Data)

Upstream product

• 118-92-3 anthranilic acid 
• 1022-46-4 2-phenyl-4H-3,1-benzoxazin-4-one 
• 249608-70-6 (2-aminophenyl)(1H-pyrrol-2-yl)methanone 
• 463-71-8 thiophosgene 
• 249608-62-6 {1-[(4-methylphenyl)sulfonyl]-1H-pyrrol-2-yl}(2-nitrophenyl)methanone 
• 249608-64-8 (2-amino-phenyl)-[1-(toluene-4-sulfonyl)-1H-pyrrol-2-yl]-methanone 

Downstream Products

• 1334215-07-4 N-[3-chloro-4-(5H-pyrrolo[1,2-c][1,3]benzodiazepin-6-(11H)-ylcarbonyl)phenyl]-5-fluoro-2-methylbenzamide 
• 1334215-09-6 N-methyl-2-(1H-pyrrol-2-ylmethyl)aniline 
• 1334215-11-0 6-(2-chloro-4-nitrobenzoyl)-6,11-dihydro-5H-pyrrolo[1,2-c][1,3]benzodiazepine 
• 1334215-12-1 3-chloro-4-(5H-pyrrolo[1,2-c][1,3]benzodiazepin-6(11H)-ylcarbonyl)aniline 

Relevant articles and documents

Synthesis of a novel pyrrolo[1,2-c][1.3]benzodiazepine analogue of VPA-985

The seven-step synthesis of a novel structural isomer of VPA-985, N-[3-chloro-4-(5H-pyrrolo[1,2-c][1.3]benzodiazepin-6(11H)-ylcarbonyl)phenyl] -5-fluoro-2-methylbenzamide, is described. (2-Aminophenyl)(1H-pyrrol-2-yl) methanone was converted with thiophosgene into (2-isothiocyanatophenyl)(1H- pyrrol-2-yl)methanone which was cyclised in the presence of base to 5-thioxo-5,6-dihydro-11H-pyrrolo[1,2-c][1.3]benzodiazepin-11-one. The latter underwent desulfurisation with Raney nickel followed by reduction with lithium aluminium hydride in the presence of aluminium trichloride and the resulting 6,11-dihydro-5H-pyrrolo[1,2-c][1.3]-benzodiazepine acylated with 2-chloro-4-nitrobenzoyl chloride to afford 6-(2-chloro-4-nitrobenzoyl)-6,11- dihydro-5H-pyrrolo[1,2-c][1.3]benzodiazepine. The nitro group in the latter compound was reduced with zinc and ammonium chloride to give the corresponding aniline derivative which was then acylated with 2-methyl-5-fluorobenzoyl chloride to provide the final product.