Acetic Acid → 5-Chloro-3-(4-methoxycarbonyl-2-thenoyl)-2-oxindole-1-carboxamide

HRID 728373Notes

Reaction equation

HRID 728373 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:10]([OH:12])=O)[S:8][CH:9]=1)=[O:4].C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[N:31]([C:35]([NH2:37])=[O:36])[C:30](=[O:38])[CH2:29]2.C(O)(=O)C>CN(C)C=O.CN(C1C=CN=CC=1)C>[Cl:25][C:26]1[CH:27]=[C:28]2[C:32](=[CH:33][CH:34]=1)[N:31]([C:35]([NH2:37])=[O:36])[C:30](=[O:38])[CH:29]2[C:10](=[O:12])[C:7]1[S:8][CH:9]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:6]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 98591595-Chloro-2-oxo-2,3-dihydro-1H-indole-1-carboxamideHCID 150073544-(Methoxycarbonyl)thiophene-2-carboxylic acid

Product 1

HCID 702224105-Chloro-3-(4-methoxycarbonyl-2-thenoyl)-2-oxindole-1-carboxamideYield 68%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×

Procedure

The title compound was prepared according to the procedure of Example 55. To a solution of 1.50 g (8.06 mmoles) of 4-methoxycarbonyl-2-thiophenecarboxylic acid (prepared as described in Example 9) in 15 ml of N,N-dimethylformamide was added 1.57 g (9.67 mmoles) of 1,1'-carbonyldiimidazole. After two hours the reaction contents were slowly added to 1.54 g (7.32 mmoles) of 5-chloro-2-oxindole-1-carboxamide and 2.66 g (21.75 mmoles) of 4-(N,N-dimethylamino)pyridine in N,N-dimethylformamide. Acidic workup of this reaction followed by filtration, drying and trituration with hot acetic acid furnished 1.88 g (4.97 mmoles, 68% yield) of title compound as a yellow solid, m.p. 244°-246° C.

Workup

  1. customThe title compound was prepared
  2. customAfter two hours the reaction contents
  3. filtrationAcidic workup of this reaction followed by filtration
  4. customdrying

Sources & evidence

ORD record
ord-79dfb5c44e0f4664ac779f8b079fb353
Source dataset
uspto-grants-1991_09
Patent number
US05047554

Reaction notes

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