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

HRID 1463504Notes

Reaction equation

HRID 1463504 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 to 1,1'-carbonyldiimidazole. The intermediate 4-chloro-2-thiophene-(l-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. 231°-3° C. (acetic acid).

Workup

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

Sources & evidence

ORD record
ord-ea34bd2df17341d4b8870439afb90b49
Source dataset
uspto-grants-1994_04
Patent number
US05300655

Reaction notes

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