Benzene → N-(alpha,alpha,2-trimethylbenzyl)-alpha-bromo-tert-butylacetamide

HRID 1577471Notes

Reaction equation

HRID 1577471 reaction equation
C1C=CC=CC=1.[CH3:7][C:8]([NH2:17])([CH3:16])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15].[Br:18][CH:19]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:20](Cl)=[O:21]>C(N(CC)CC)C>[CH3:16][C:8]([NH:17][C:20](=[O:21])[CH:19]([C:23]([CH3:26])([CH3:25])[CH3:24])[Br:18])([CH3:7])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15]

Participants

5

Reactant 3

HCID 241BenzeneHCID 108676212-Bromo-3,3-dimethylbutanoyl chlorideHCID 130256632-(O-tolyl)propan-2-amine

Product 1

HCID 12760503N-(alpha,alpha,2-trimethylbenzyl)-alpha-bromo-tert-butylacetamideYield 88.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Into a 200 ml four-necked flask, there were charged benzene (150 ml), α,α,2-trimethylbenzylamine (7.5 g) and triethylamine (6 g), and α-bromo-tert-butylacetyl chloride (10.2 g) was dropwise added thereto while stirring at room temperature. Stirring was continued for 3 hours. After completion of the reaction, the reaction mixture was washed with water to remove triethylamine hydrochloride. The benzene layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was recrystallized from ethanol to give 13.8 g of N-(α,α,2-trimethylbenzyl)-α-bromo-tert-butylacetamide. M.P., 166.5°-168° C.

Workup

  1. additionwas dropwise added
  2. stirringStirring
  3. customAfter completion of the reaction
  4. washthe reaction mixture was washed with water
  5. customto remove triethylamine hydrochloride
  6. dry with materialThe benzene layer was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-668c701e32d64bc8bbdf8606646df2e6
Source dataset
uspto-grants-1981_09
Patent number
US04288244

Reaction notes

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