Sodium borohydride → 1-(4-Chlorophenoxy)-4-(4-chlorophenylmercapto)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-ol

HRID 1995926Notes

Reaction equation

HRID 1995926 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:30]=[CH:29][C:7]([O:8][CH:9]([N:24]2[CH:28]=[N:27][CH:26]=[N:25]2)[C:10](=[O:23])[C:11]([CH3:22])([CH3:21])[CH2:12][S:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[CH:6][CH:5]=1>O.CO>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH:9]([N:24]2[CH:28]=[N:27][CH:26]=[N:25]2)[CH:10]([OH:23])[C:11]([CH3:22])([CH3:21])[CH2:12][S:13][C:14]2[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=2)=[CH:29][CH:30]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 12765983HCID 12765983, compound

Product 1

HCID 127659911-(4-Chlorophenoxy)-4-(4-chlorophenylmercapto)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-olYield 54.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

0.35 g (0.0092 mol) of sodium borohydride in 8 ml of water was added in portions to 10 g (0.023 mol) of 1-(4-chlorophenoxy)-4-(4-chlorophenylmercapto)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one (Example 4e) in 200 ml of methanol. The reaction mixture was subsequently stirred at 20° C. for 4 hours, poured onto water and extracted with ether. The ether phase was dried over sodium sulphate and concentrated. 5.5 g (54.6% of theory) of 1-(4-chlorophenoxy)-4-(4-chlorophenylmercapto)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-ol of melting point 132° C. were obtained.

Workup

  1. additionpoured onto water
  2. extractionextracted with ether
  3. dry with materialThe ether phase was dried over sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-48dcddfac4a242e293606a5dae570bd9
Source dataset
uspto-grants-1983_09
Patent number
US04406909

Reaction notes

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