Acetonitrile → 5,6-Dimethoxy-2-oxindole-1-carboxamide

HRID 637350Notes

Reaction equation

HRID 637350 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[NH:8][C:7](=[O:14])[CH2:6]2.ClS([N:19]=[C:20]=[O:21])(=O)=O.C(#N)C>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]([C:20]([NH2:19])=[O:21])[C:7](=[O:14])[CH2:6]2

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 70918Chlorosulfonyl isocyanateHCID 2229935,6-Dimethoxyindolin-2-one

Product 1

HCID 136476345,6-Dimethoxy-2-oxindole-1-carboxamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Following the procedure of Example 24, the title compound was prepared from 5,6-dimethoxy-2-oxindole (8.0 g, 0.042 mole), chlorosulfonyl isocyanate (7.08 g, 0.05 mole) and acetonitrile (75 ml). The crude product obtained upon evaporation of the ethyl acetate extract was recrystallized from acetonitrile/acetic acid (1:1). Yield=6.02 g (60%); m.p. 206.5°-209° C.

Sources & evidence

ORD record
ord-761d4e2d0bf44d76915af218d1429282
Source dataset
uspto-grants-1985_12
Patent number
US04556672

Reaction notes

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