Methyl iodide → 1-Methyl-6-(4-phenylmercapto-butoxy)-3,4-dihydro-carbostyril

HRID 1065349Notes

Reaction equation

HRID 1065349 reaction equation
[C:1]1([S:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[NH:19][C:18](=[O:23])[CH2:17][CH2:16]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:26]I>CN(C)C=O.O>[CH3:26][N:19]1[C:20]2[C:15](=[CH:14][C:13]([O:12][CH2:11][CH2:10][CH2:9][CH2:8][S:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:22][CH:21]=2)[CH2:16][CH2:17][C:18]1=[O:23]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 248459066-(4-Phenylmercapto-butoxy)-3,4-dihydro-carbostyril

Product 1

HCID 539875161-Methyl-6-(4-phenylmercapto-butoxy)-3,4-dihydro-carbostyril

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

16.2 gm of 6-(4-phenylmercapto-butoxy)-3,4-dihydro-carbostyril were dissolved in 100 ml of dimethylformamide, and 4.8 gm of a 50% sodium hydride suspension in paraffin oil were added to this solution. After addition of 12.5 ml of methyl iodide, the mixture was stirred for 3 hours at room temperature, diluted with water and extracted with chloroform. The evaporation residue of the chloroform extract was recrystallized with methanol in the presence of activated charcoal.

Workup

  1. extractionextracted with chloroform
  2. extractionThe evaporation residue of the chloroform extract
  3. customwas recrystallized with methanol in the presence of activated charcoal

Sources & evidence

ORD record
ord-5b8012e57167458399dc9e0085829a52
Source dataset
uspto-grants-1982_05
Patent number
US04329347

Reaction notes

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