Water → HCID 18973041, compound

HRID 2394360Notes

Reaction equation

HRID 2394360 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](=[O:19])[C:13]1[S:17][CH:16]=[C:15]([CH3:18])[CH:14]=1.[C:20](=[O:26])=[N:21]S(Cl)(=O)=O.C(#N)C.O>CS(C)=O>[Cl:1][C:2]1[N:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:20]([NH2:21])=[O:26])[C:6](=[O:11])[CH:5]2[C:12](=[O:19])[C:13]1[S:17][CH:16]=[C:15]([CH3:18])[CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 70918Chlorosulfonyl isocyanate2×HCID 18973028HCID 18973028, compound2×

Product 1

HCID 18973041HCID 18973041, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was prepared from 5-chloro-3-(4-methyl-2-thenoyl)-4-azaoxindole (Example 30) according to the procedure of Example 2C, using 5-chloro-3-(4-methyl-2-thenoyl)-4-azaoxindole (0.90 g, 3.07 mmol), N-chlorosulfonyl isocyanate (0.40 mL, 4.60 mmol), and acetonitrile (15 mL). The crude N-chlorosulfonyl isocyanate was hydrolyzed by stirring in DMSO in a flask open to the air. The product was isolated by dilution with water and filtration, and was recrystallized from acetic acid. Yield: 190 mg (18%). M.P. 227°-228° C.

Workup

  1. customwas recrystallized from acetic acid

Sources & evidence

ORD record
ord-cb867a9c34ec42a4a7296b045d4a5a82
Source dataset
uspto-grants-1998_09
Patent number
US05811432

Reaction notes

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