5-Chloro-2-oxo-2,3-dihydro-1H-indole-1-carboxamide → 5-Chloro-3-(4-methoxy-2-thenoyl)-2-oxindole-1-carboxamide

HRID 566210Notes

Reaction equation

HRID 566210 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:8]([OH:10])=O)[S:6][CH:7]=1.[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([C:21]([NH2:23])=[O:22])[C:16](=[O:24])[CH2:15]2>CN(C1C=CN=CC=1)C.S(Cl)(Cl)=O>[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([C:21]([NH2:23])=[O:22])[C:16](=[O:24])[CH:15]2[C:8](=[O:10])[C:5]1[S:6][CH:7]=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

5

Reactant 2

HCID 98591595-Chloro-2-oxo-2,3-dihydro-1H-indole-1-carboxamideHCID 126466194-Methoxythiophene-2-carboxylic acid

Product 1

HCID 702186055-Chloro-3-(4-methoxy-2-thenoyl)-2-oxindole-1-carboxamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 24386Thionyl ChlorideSolvent

Procedure

The title compound was prepared according to the procedure of Example 32. A 1.30 g (8.22 mmoles) sample of 4-methoxy-2-thiophenecarboxylic acid (prepared according to Gronowitz, S., Arkiv. for Kemi. 12:239 (1958)) was converted to 1.19 g of pure acid chloride (b.p. 58-60° C., 0.03 mm) with 10 ml of thionyl chloride. The acid chloride was coupled to 1.18 g (5.61 mmoles) of 5-chloro-2-oxindole-1-carboxamide in the presence of 1.73 g (14.15 mmoles) 4-(N,N-dimethylamino)pyridine to give 1.88 g of crude product on acidic workup. Recrystallization gave 1.39 g (3.96 mmoles, 71% yield) of pure 5-chloro-3-(4-methoxy-2-thenoyl)-2-oxindole-1-carboxamide as a yellow solid, m.p. 221-223° C. (acetic acid).

Workup

  1. customto give 1.88 g of crude product on acidic workup

Sources & evidence

ORD record
ord-b09f27d0fc6f45c5b3e386fb033b0f8d
Source dataset
uspto-grants-2001_01
Patent number
US06174883B1

Reaction notes

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