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

HRID 486157Notes

Reaction equation

HRID 486157 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.[N-]1C=CN=C1.[N:27]1([C:37]([NH2:39])=[O:38])[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29][C:28]1=[O:36]>CN(C)C=O.CN(C1C=CN=CC=1)C.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:7]([CH:29]2[C:30]3[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=3)[N:27]([C:37]([NH2:39])=[O:38])[C:28]2=[O:36])=[O:9])[S:5][CH:6]=1

Participants

8

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 3386966ImidazolateHCID 115172742-Oxindole-1-carboxamideHCID 122906954-Chlorothiophene-2-carboxylic acid

Product 1

HCID 99051743-(4-Chloro-2-thenoyl)-2-oxindole-1-carboxamide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to the procedure of Example 55. An 831 mg (5.11 mmole) portion of 4-chloro-2-thiophenecarboxylic acid (prepared according to Iriarte, J., et al., J. Het. Chem., 13, 393 (1976)) was combined with 897 mg (5.53 mmole) of 1,1'-carbonyldiimidazole in 5 ml of N,N-dimethylformamide and the intermediate imidazolide coupled directly with 750 mg (4.26 mmole) of 2-oxindole-1-carboxamide in the presence of 1.40 g (11.49 mmole) of 4-(N,N-dimethylamino)pyridine. The resulting crude yellow solid (803 mg, 59% yield) was recrystallized from acetic acid to furnish 376 mg (1.17 mmole, 27% yield) of fluffy yellow crystals, m.p. 221°-3° C.

Sources & evidence

ORD record
ord-324403d442e54561acf727dc10d64a3f
Source dataset
uspto-grants-1994_03
Patent number
US05290802

Reaction notes

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