Potassium Cyanide → N'-(3-chloro-5-fluoro-4-(hydroxymethyl)phenylsulfonyl)-N,N-dimethylformimidamide
Reaction equation
[C-]#N.[K+].C([O:7][CH2:8][C:9]1[C:14]([F:15])=[CH:13][C:12]([S:16](=[O:23])(=[O:22])[N:17]=[CH:18][N:19]([CH3:21])[CH3:20])=[CH:11][C:10]=1[Cl:24])(=O)C>CO>[Cl:24][C:10]1[CH:11]=[C:12]([S:16]([N:17]=[CH:18][N:19]([CH3:21])[CH3:20])(=[O:22])=[O:23])[CH:13]=[C:14]([F:15])[C:9]=1[CH2:8][OH:7]Participants
4
Procedure
To a solution of KCN (82 mg, 1.26 mmol) in MeOH (80 mL) was added 2-chloro-4-(N-((dimethylamino)methylene)sulfamoyl)-6-fluorobenzyl acetate (850 mg, 2.52 mmol) at 0° C. The mixture was allowed to attain room temperature and then refluxed 1 h. After cooling, the reaction mixture was quenched with H2O, concentrated, and extracted with EtOAc. The combined extracts were washed with brine, dried over anhyd MgSO4, filtered and concentrated under reduced pressure to give N′-(3-chloro-5-fluoro-4-(hydroxymethyl)phenylsulfonyl)-N,N-dimethylformimidamide (600 mg, 80%) as ivory solid. 1H NMR (400 MHz, CDCl3) δ 8.10(s, 1H), 7.74 (s, 1H), 7.55 (d, 1H), 4.86 (d, 2H), 3.17 (s, 3H), 3.05 (s, 3H), 2.07 (s, 1H).