Water → HCID 22761227, compound

HRID 1703440Notes

Reaction equation

HRID 1703440 reaction equation
[C:1]([NH:9][CH:10]([N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1)[C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O>CO>[C:1]([NH:9][CH:10]([N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1)[CH:11]([OH:16])[C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 22761232N-[1-(1H-Imidazol-1-yl)-3,3-dimethyl-2-oxobutyl]benzamide

Product 1

HCID 22761227HCID 22761227, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Process variant (b) 28.5 g (0.1 mol) of 1-benzamido-3,3-dimethyl-1-(imidazol-1-yl)-butan-2-one of melting point 140°-142° C. (prepared analogously to Example 8, in accordance with process (a)) were dissolved in 250 ml of methanol. 4 g (0.1 mol) of sodium borohydride were added in portions while stirring and cooling at 0° to 10° C. Stirring was continued for 15 hours at room temperature and 200 ml of water were added to the reaction mixture. The mixture was then extracted by shaking with 200 ml of methylene chloride and the organic phase as dried over sodium sulphate and concentrated by distilling off the solvent in vacuo. Boiling up with petroleum ether and a little ether caused the mixture to crystallize. 22.6 g (79% of theory) of 1-benzamido-3,3-dimethyl-1-imidazol-1-yl-butan-2-ol of melting point 143° C. were obtained.

Workup

  1. temperaturecooling at 0° to 10° C
  2. stirringStirring
  3. extractionThe mixture was then extracted
  4. stirringby shaking with 200 ml of methylene chloride
  5. dry with materialthe organic phase as dried over sodium sulphate
  6. concentrationconcentrated
  7. distillationby distilling off the solvent in vacuo
  8. customto crystallize

Sources & evidence

ORD record
ord-255d753c54d94180ab816e18f65ef0cb
Source dataset
uspto-grants-1978_11
Patent number
US04124369

Reaction notes

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