Chlorosulfonyl isocyanate → N-chlorosulfonyl-2-oxindole-1-carboxamide

HRID 637339Notes

Reaction equation

[N:1]1([C:11]([NH2:13])=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].N1C2C(=CC=CC=2)CC1=O.[Cl:24][S:25](N=C=O)(=[O:27])=[O:26]>>[Cl:24][S:25]([NH:13][C:11]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10])=[O:12])(=[O:27])=[O:26]

Participants

Reactant 3

HCID 70918Chlorosulfonyl isocyanate

HCID 321710Oxindole

HCID 115172742-Oxindole-1-carboxamide

Product 1

HCID 13854225N-chlorosulfonyl-2-oxindole-1-carboxamide

Procedure

In the second method for preparing the 2-oxindole-1-carboxamide compounds of the formula II, a 2-oxindole of the formula VI is reacted with chlorosulfonyl isocyanate to give the intermediate N-chlorosulfonyl-2-oxindole-1-carboxamide of formula VII, followed by removal of the chlorosulfonyl group by hydrolysis, viz., ##STR10##

Sources & evidence

ORD record: ord-38c75f3a41f843eab86c02b4a529561a
Source dataset: uspto-grants-1985_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04556672

Reaction notes

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