Methyl Isobutyl Ketone → N-(alpha,alpha-dimethylbenzyl)-alpha-bromo-isovaleramide

HRID 1680607Notes

Reaction equation

HRID 1680607 reaction equation
CC(CC(C)C)=O.[CH3:8][C:9]([NH2:17])([CH3:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.[Br:25][CH:26]([CH:30]([CH3:32])[CH3:31])[C:27](Cl)=[O:28]>O>[CH3:8][C:9]([NH:17][C:27](=[O:28])[CH:26]([Br:25])[CH:30]([CH3:32])[CH3:31])([CH3:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 7909Methyl Isobutyl KetoneHCID 8471TriethylamineHCID 68509CumylamineHCID 124869822-Bromo-3-methylbutanoyl chloride

Product 1

HCID 12895705N-(alpha,alpha-dimethylbenzyl)-alpha-bromo-isovaleramideYield 87.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 500 ml four-necked flask, there were charged methylisobutylketone (150 ml), α,α-dimethylbenzylamine (27.0 g) and triethylamine (21.2 g), and α-bromo-isovaleryl chloride (40.0 g) was dropwise added thereto while stirring at room temperature. Stirring was continued for 3 hours. After completion of the reaction, water (200 ml) was added thereto and the reaction mixture was gradually heated to remove methylisobutylketone, followed by cooling at room temperature. The precipitated crystals were filtered, washed with water, dried and recrystallized from ethanol to give N-(α,α-dimethylbenzyl)-α-bromo-isovaleramide (51.9 g).

Workup

  1. additionwas dropwise added
  2. stirringStirring
  3. additionwas added
  4. temperaturethe reaction mixture was gradually heated
  5. customto remove methylisobutylketone
  6. temperatureby cooling at room temperature
  7. filtrationThe precipitated crystals were filtered
  8. washwashed with water
  9. customdried
  10. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-2da2347d7f1e4112801853393bc0520d
Source dataset
uspto-grants-1981_06
Patent number
US04274862

Reaction notes

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