Chloroacetamide → HCID 21484732, compound

HRID 1414697Notes

Reaction equation

[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH:8][C:7]([Cl:17])=[CH:6][CH:5]=2.[H-].[Na+].Cl[CH2:21][C:22]([NH2:24])=[O:23]>O.CN(C)C=O.C1(C)C=CC=CC=1>[C:22]([CH2:21][N:3]1[C:4]2[C:9](=[CH:8][C:7]([Cl:17])=[CH:6][CH:5]=2)[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:2]1[CH3:1])(=[O:23])[NH2:24]

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 3 g. of 2-methyl-3-phenyl-5-chloro-indole in a solvent mixture 7 ml. of toluene and 5 ml. of dimethylformamide is added to a suspension of 0.6 g. of 50% sodium hydride (in paraffin) in 5 ml. of toluene at 20° C. After the reaction mixture is stirred at 20° C. for one hour, a solution of 1.1 g. of chloroacetamide in 20 ml. of dimethylformamide is added thereto at 20° C., and the reaction mixture is stirred under reflux for 5 hours. The resultant mixture is diluted with water and is extracted with benzene. The organic layer is washed with water and dried over sodium sulfate. The solvent is removed to a residue, which is recrystallized from ethanol to give 1-carbamoylmethyl-2-methyl-3-phenyl-5-chloroindole, m.p. 223°-224° C.

Workup

customat 20° C
stirringat 20° C., and the reaction mixture is stirred
temperatureunder reflux for 5 hours
extractionis extracted with benzene
washThe organic layer is washed with water
dry with materialdried over sodium sulfate
customThe solvent is removed to a residue, which
customis recrystallized from ethanol

Sources & evidence

ORD record: ord-5f02f1394fec46138d3b188990371899
Source dataset: uspto-grants-1977_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04002611

Reaction notes

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