Hydrochloric Acid → 5-chloro-2-oxo-3-(thiophene-2-carbonyl)-3H-indole-1-carboxamide

HRID 1906578Notes

Reaction equation

HRID 1906578 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([NH2:13])=[O:12])[C:6](=[O:14])[CH2:5]2.[C:15]1([C:20](Cl)=[O:21])[S:19][CH:18]=[CH:17][CH:16]=1.O.Cl>CN(C1C=CN=CC=1)C.CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([NH2:13])=[O:12])[C:6](=[O:14])[CH:5]2[C:20](=[O:21])[C:15]1[S:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 789282-Thiophenecarbonyl chlorideHCID 98591595-Chloro-2-oxo-2,3-dihydro-1H-indole-1-carboxamide

Product 1

HCID 579465-chloro-2-oxo-3-(thiophene-2-carbonyl)-3H-indole-1-carboxamideYield 82.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×

Procedure

A stirred slurry of 21.1 g (0.1 mole) of 5-chloro-2-oxindole-1-carboxamide and 26.9 g (0.22 mole) of 4-(N,N-dimethylamino)pyridine in 200 ml of N,N-dimethylformamide was cooled to ice-bath temperature, and then a solution of 16.1 g (0.11 mole) of 2-thenoyl chloride in 50 ml of N,N-dimethylformamide was added dropwise. Stirring was continued for ca. 30 minutes, and then the reaction mixture was poured into a mixture of 1 liter of water and 75 ml of 3N hydrochloric acid. The resulting mixture was cooled in an ice-bath, and then the solid was collected by filtration. The solid was recrystallized from 1800 ml of acetic acid to give 26.6 g of the title compound as fluffy, yellow crystals, m.p. 230° C. (dec.).

Workup

  1. temperatureThe resulting mixture was cooled in an ice-bath
  2. filtrationthe solid was collected by filtration
  3. customThe solid was recrystallized from 1800 ml of acetic acid

Sources & evidence

ORD record
ord-894c77ec316e40f29c37604d8f3cf0b2
Source dataset
uspto-grants-1987_03
Patent number
US04652658

Reaction notes

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