1,1'-Carbonyldiimidazole → 6-Chloro-3-(4-chloro-2-thenoyl)-2-oxindole-1-carboxamide

HRID 486156Notes

Reaction equation

HRID 486156 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:7]([OH:9])=O)[S:5][CH:6]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:22][C:23]1[CH:31]=[C:30]2[C:26]([CH2:27][C:28](=[O:35])[N:29]2[C:32]([NH2:34])=[O:33])=[CH:25][CH:24]=1>CN(C1C=CN=CC=1)C.C(O)(=O)C>[Cl:22][C:23]1[CH:31]=[C:30]2[C:26]([CH:27]([C:7](=[O:9])[C:4]3[S:5][CH:6]=[C:2]([Cl:1])[CH:3]=3)[C:28](=[O:35])[N:29]2[C:32]([NH2:34])=[O:33])=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 122906954-Chlorothiophene-2-carboxylic acidHCID 136476276-Chloro-2-oxindole-1-carboxamide

Product 1

HCID 98849686-Chloro-3-(4-chloro-2-thenoyl)-2-oxindole-1-carboxamideYield 53%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 176Acetic AcidSolvent

Procedure

The experimental procedure used to produce the title compound was adopted from Example 55. A 463 mg (2.85 mmole) portion of 4-chloro-2-thiophenecarboxylic acid (prepared according to Iriarte, J., et al., J. Het. Chem., 13, 393 (1976)) was transformed into the acyl imidazole by reaction with 500 mg (3.09 mmole) of 1,1'-carbonyldiimidazole. The intermediate 4-chloro-2-thiophene-(1-imidazo)carboxamide coupled directly with 500 mg (2.37 mmole) of 6-chloro-2-oxindole-1-carboxamide in the presence of 783 mg (6.41 mmole) of 4-(N,N-dimethylamino)pyridine to give 665 mg of crude greenish-yellow solid. Recrystallization gave 450 mg (1.27 mmole, 53% yield) of pure title compound as a yellow solid, m.p. 23°-3° C. (acetic acid).

Workup

  1. customto give 665 mg of crude greenish-yellow solid
  2. customRecrystallization

Sources & evidence

ORD record
ord-e8ea42e288d24deabad007298b993672
Source dataset
uspto-grants-1994_03
Patent number
US05290802

Reaction notes

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