5-Chloro-2-oxo-2,3-dihydro-1H-indole-1-carboxamide → HCID 70221621, compound

HRID 728370Notes

Reaction equation

HRID 728370 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([NH2:13])=[O:12])[C:6](=[O:14])[CH2:5]2.[CH3:15][S:16]([C:19]1[S:23][C:22]([C:24](Cl)=[O:25])=[CH:21][CH:20]=1)(=[O:18])=[O:17]>CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([NH2:13])=[O:12])[C:6](=[O:14])[CH:5]2[C:24](=[O:25])[C:22]1[S:23][C:19]([S:16]([CH3:15])(=[O:18])=[O:17])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 98591595-Chloro-2-oxo-2,3-dihydro-1H-indole-1-carboxamideHCID 12836074HCID 12836074, compound

Product 1

HCID 70221621HCID 70221621, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

The title compound was prepared according to the procedure of Example 32. A 2.06 g (10.0 mmoles) sample of 5-methylsulfonyl-2-thiophenecarboxylic acid (prepared according to Cymerman-Craig, J., et al., J. Chem. Soc.:237 (1954)) reacted with 10 ml of thionyl chloride to give 2.14 g of crude acid chloride as a solid. The reaction of 1.75 g (8.33 mmoles) of 5-chloro-2-oxindole-1-carboxamide with 5-methylsulfonyl-2-thiophenecarbonyl chloride in the presence of 3.05 g (25.0 mmoles) of 4-(N,N-dimethylamino)pyridine gave 3.17 g of crude product after acidic workup. A single recrystallization from acetic acid gave 2.31 g (5.80 mmoles, 70% yield) of pure 5-chloro-3-(5-methylsulfonyl-2-thenoyl)-2-oxindole-1-carboxamide as a deep-orange solid, m.p. 212°-14° C.

Workup

  1. customgave 3.17 g of crude product after acidic workup
  2. customA single recrystallization from acetic acid

Sources & evidence

ORD record
ord-9eabcc46d73147ebbf4b1ce6da1f275c
Source dataset
uspto-grants-1991_09
Patent number
US05047554

Reaction notes

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