Sodium borohydride → 4-(4-Chlorophenylmercapto)-3,3-dimethyl-1-(imidazol-1-yl)-butan-2-ol

HRID 1199900Notes

Reaction equation

HRID 1199900 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:11][C:12]([CH3:22])([CH3:21])[C:13](=[O:20])[CH2:14][N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)=[CH:6][CH:5]=1.BrCC(=O)C(C)(C)CSC1C=CC(Cl)=CC=1>O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:11][C:12]([CH3:22])([CH3:21])[CH:13]([OH:20])[CH2:14][N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 127659741-Bromo-4-[(4-chlorophenyl)sulfanyl]-3,3-dimethylbutan-2-oneHCID 130649584-[(4-Chlorophenyl)sulfanyl]-1-(1H-imidazol-1-yl)-3,3-dimethylbutan-2-one

Product 1

HCID 130649594-(4-Chlorophenylmercapto)-3,3-dimethyl-1-(imidazol-1-yl)-butan-2-olYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.3 g (0.0079 mol) of sodium borohydride in 8 ml of water was added dropwise to 7 g (0.024 mol) of 4-(4-chlorophenylmercapto)-3,3-dimethyl-1-(imidazol-1-yl)-butan-2-one, compound 6 of Example 6 hereinabove, at room temperature. The reaction mixture was subsequently stirred at room temperature for 1 hour and was poured onto water. The crystals which had precipitated were filtered off, and dried at 50° C. in vacuo. 6.5 g (91% of theory) of 4-(4-chlorophenylmercapto)-3,3-dimethyl-1-(imidazol-1-yl)-butan-2-ol of melting point 109°-110° C. were obtained.

Workup

  1. additionwas poured onto water
  2. customThe crystals which had precipitated
  3. filtrationwere filtered off
  4. customdried at 50° C. in vacuo

Sources & evidence

ORD record
ord-0dd67543f4b34edea814c661c0add1a6
Source dataset
uspto-grants-1990_02
Patent number
US04904297

Reaction notes

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