Methyl iodide → HCID 14054339, compound

HRID 1382859Notes

Reaction equation

HRID 1382859 reaction equation
[OH-].[K+].[CH3:3][CH:4]([NH:7][C:8]([C:10]1[CH:11]=[C:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:17]=[CH:16][S:15][C:14]=2[CH:18]=1)=[O:9])[CH2:5][CH3:6].[CH3:25]I>CS(C)=O>[CH3:25][N:7]([CH:4]([CH3:3])[CH2:5][CH3:6])[C:8]([C:10]1[CH:11]=[C:12]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:13]2[CH:17]=[CH:16][S:15][C:14]=2[CH:18]=1)=[O:9]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 21273351HCID 21273351, compound

Product 1

HCID 14054339HCID 14054339, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The reaction is carried out as in Example 2, starting with dimethyl sulfoxide (24 cc), potassium hydroxide powder (3.6 g), N-(1-methylpropyl)-4-phenylbenzo[b]thiophene-6-carboxamide (4 g) and methyl iodide (1.6 cc). After chromatography of the residue over silica gel using a cyclohexane:ethyl acetate (50:50 by volume) mixture as the eluent and recrystallization in isopropyl ether, N-methyl-N-(1-methylpropyl)-4-phenylbenzo[b]thiophene-6-carboxamide (1.2 g), m.p. 84° C., is isolated.

Workup

  1. customAfter chromatography of the residue over silica gel using a cyclohexane:ethyl acetate (50:50 by volume) mixture as the eluent and recrystallization in isopropyl ether

Sources & evidence

ORD record
ord-a53519714b204223a8ca8b9627a7ded4
Source dataset
uspto-grants-1989_02
Patent number
US04808599

Reaction notes

Loading…