Dimethyl Disulfide → HCID 22259330, compound

HRID 1610951Notes

Reaction equation

HRID 1610951 reaction equation
CS[S:3][CH3:4].C(P(CCCC)CCCC)CCC.[C:18]([O:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][CH2:31][CH2:32][N:33]2[CH:37]=[CH:36][N:35]=[C:34]2[CH2:38]O)=[CH:25][CH:24]=1)([CH3:21])([CH3:20])[CH3:19]>N1C=CC=CC=1.C(OCC)(=O)C>[C:18]([O:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][CH2:31][CH2:32][N:33]2[CH:37]=[CH:36][N:35]=[C:34]2[CH2:38][S:3][CH3:4])=[CH:25][CH:24]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 12232Dimethyl DisulfideHCID 13831TributylphosphineHCID 22259320HCID 22259320, compound

Product 1

HCID 22259330HCID 22259330, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dimethyl disulfide (8.94 ml) and tributylphosphine (24.7 ml) were added to a solution of [1-[4-(4-tert-butoxyphenyl)butyl]-1H-imidazol-2-yl]methanol (10.0 g) in pyridine (13.4 ml) at room temperature, and the mixture was stirred at room temperature for 17 hr. The reaction mixture was diluted with ethyl acetate, successively washed with 1N aqueous sodium hydroxide solution (3 times) and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give crude 1-[4-(4-tert-butoxyphenyl)butyl]-2-[(methylthio)methyl]-1H-imidazole. 4N Hydrochloric acid (33 ml) was added to the product, and the mixture was stirred at 50° C. for 2 hr. After cooling, the reaction mixture was combined with water and ethyl acetate and separated. The water layer was adjusted to pH 6 by adding 30% aqueous sodium hydroxide solution to salt out and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was washed with diisopropyl ether to give the titled compound (7.31 g) as a colorless crystal powder.

Workup

  1. washsuccessively washed with 1N aqueous sodium hydroxide solution (3 times) and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-fb5cf7df429647bba0676be51653f8ac
Source dataset
uspto-grants-2006_01
Patent number
US06984653B2

Reaction notes

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