1-Pyrrolidinecarbonyl chloride → HCID 18415666, compound

Reaction equation

[Br:1][C:2]([F:12])([F:11])[S:3]([C:6]1[N:10]=[CH:9][NH:8][N:7]=1)(=[O:5])=[O:4].[N:13]1([C:18](Cl)=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14]1>N1C=CC=CC=1.O>[Br:1][C:2]([F:11])([F:12])[S:3]([C:6]1[N:10]=[CH:9][N:8]([C:18]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:19])[N:7]=1)(=[O:4])=[O:5]

Participants

Procedure

To a solution of 0.12 g (0.45 mmol) 3-(bromodifluoromethylsulfonyl)-1,2,4-triazole, prepared as above, in 0.5 ml dry pyridine was added 0.07 g (0.54 mmol) pyrrolidine-1-carbonyl chloride and the mixture was agitated for 16 h at room temperature. The reaction mixture was then diluted with water and extracted with ether. The resulting organic layer was washed successively with dilute hydrochloric acid, water and saturated sodium bicarbonate solution, dried over MgSO4 and evaporated to give 0.1 g (65% yield) of the desired 3-(bromodifluoromethylsulfonyl)-1-(pyrrolidinocarbonyl)-1,2,4-triazole as a pale yellow oil: 1H NMR (CDCl3) δ(ppm) 9.1 (1H), 4.0 (2H), 3.7 (2H), 2.1 (4H).