2-Bromopropane → 1-(1-Methylethyl)-6-(methylthio)-benz[cd]indol-2(1H)-one

HRID 484102Notes

Reaction equation

HRID 484102 reaction equation
[CH3:1][S:2][C:3]1[C:4]2[C:5]3[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]=3[CH:13]=[CH:14][CH:15]=2.[H-].[Na+].Br[CH:19]([CH3:21])[CH3:20]>CN(C)C=O>[CH3:20][CH:19]([N:8]1[C:9]2[C:5]3[C:4](=[CH:15][CH:14]=[CH:13][C:6]=3[C:7]1=[O:12])[C:3]([S:2][CH3:1])=[CH:11][CH:10]=2)[CH3:21]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 24758Sodium hydrideHCID 197508246-(Methylthio)benz[cd]indol-2(1H)-one

Product 1

HCID 197508171-(1-Methylethyl)-6-(methylthio)-benz[cd]indol-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.0 g of 6-(methylthio)-benz[cd]indol-2(1H)-one (Example 2), 0.48 g of 60% sodium hydride and 2.33 ml of 2-bromopropane in 100 ml of N,N-dimethylformamide is reacted for 23 hours using the conditions of Example 4 to yield 1.15 g of the desired product as a bright yellow solid, m.p. 70°-71° C.

Workup

  1. customis reacted for 23 hours

Sources & evidence

ORD record
ord-d5950ed189b64f3ab3497dc8500e9eaf
Source dataset
uspto-grants-1993_07
Patent number
US05229411

Reaction notes

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