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

HRID 637342Notes

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.Cl.O>CN(C)C=O.CN(C1C=CN=CC=1)C>[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

Conditions

Temperature: 8 °C

Procedure

To a stirred solution of 429.9 g (2.04 mole) of 5-chloro-2-oxindole-1-carboxamide in 4 liters of N,N-dimethylformamide was added 547.9g (4.48 mole) of 4-(N,N-dimethylamino)pyridine, and then the mixture was cooled to 8° C. To this mixture was added, with stirring, a solution of 328 g (2.23 mole) of thenoyl chloride in 800 ml N,N-dimethylformamide over a 30 minute period, with the temperature being maintained between 8° and 15° C. Stirring was continued for 30 minutes, and then the reaction mixture was poured with stirring into a mixture of 510 ml of concentrated hydrochloric acid and 12 liters of water. Stirring was continued for 2 hours, and then the solid was collected by filtration and washed with water followed by methanol. The solid was dried to give 675.6 g of the title compound.

Workup

additionTo this mixture was added
temperaturewith the temperature being maintained between 8° and 15° C
stirringStirring
additionthe reaction mixture was poured
stirringStirring
waitwas continued for 2 hours
filtrationthe solid was collected by filtration
washwashed with water
customThe solid was dried

Sources & evidence

ORD record: ord-06946e869b204998998803cd02eceecf
Source dataset: uspto-grants-1985_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04556672

Reaction notes

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