Acetonitrile → HCID 18973079, compound

HRID 2394369Notes

Reaction equation

HRID 2394369 reaction equation
[C:1]([CH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([Cl:18])[N:16]=2)[NH:11][C:10]1=[O:19])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20](=[O:26])=[N:21]S(Cl)(=O)=O.C(#N)C.ClS(NC=O)(=O)=O>CS(C)=O>[C:1]([CH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([Cl:18])[N:16]=2)[N:11]([C:20]([NH2:21])=[O:26])[C:10]1=[O:19])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 70918Chlorosulfonyl isocyanateHCID 15228322HCID 15228322, compoundHCID 18973030HCID 18973030, compound2×

Product 1

HCID 18973079HCID 18973079, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was prepared from 3-benzoyl-5-chloro-4-azaoxindole (Example 32) according to the procedure of Example 25, using 3-benzoyl-5-chloro-4-azaoxindole (2.73 g, 10.0 mmol), N-chlorosulfonyl isocyanate (1.3 mL, 15 mmol) and acetonitrile (80 mL). The reaction time was 20 hours. The crude N-chlorosulfonyl carboxamide was hydrolyzed by stirring in DMSO (15 mL) for 20 hours. The crude product was recrystallized from acetic acid and washed with methanol. Yield: 0.36 g (11%).

Workup

  1. customThe crude product was recrystallized from acetic acid
  2. washwashed with methanol

Sources & evidence

ORD record
ord-346b5894a84249f29e7858d02daf1ef1
Source dataset
uspto-grants-1998_09
Patent number
US05811432

Reaction notes

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