Chlorosulfonyl isocyanate → HCID 18973107, compound

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH:5]2[C:12]([C:14]1[O:15][CH:16]=[CH:17][CH:18]=1)=[O:13].[C:19](=[O:25])=[N:20]S(Cl)(=O)=O.ClS(NC=O)(=O)=O>C(#N)C>[Cl:1][C:2]1[N:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:19]([NH2:20])=[O:25])[C:6](=[O:11])[CH:5]2[C:12]([C:14]1[O:15][CH:16]=[CH:17][CH:18]=1)=[O:13]

Participants

Procedure

The title compound was prepared from 5-chloro-3-(2-furoyl)-4-azaoxindole (Example 23) according to the procedure of Example 2C, using 5-chloro-3-(2-furoyl)-4-azaoxindole (200 mg, 0.76 mmol), N-chlorosulfonyl isocyanate (0.10 mL, 1.1 mmol) and acetonitrile (8 mL). Hydrolysis of the N-chlorosulfonyl carboxamide was achieved by quenching the above reaction with water and allowing the mixture to stir at room temperature overnight. The product was collected by filtration and recrystallized from DMSO. Yield: 75 mg (32%).