Benzene → HCID 12760502, compound

HRID 1577470Notes

Reaction equation

HRID 1577470 reaction equation
C1C=CC=CC=1.[CH3:7][C:8]([NH2:16])([CH3:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Br:17][CH:18]([C:22]([CH2:25][CH3:26])([CH3:24])[CH3:23])[C:19](Cl)=[O:20]>C(N(CC)CC)C>[CH3:7][C:8]([NH:16][C:19](=[O:20])[CH:18]([C:22]([CH2:25][CH3:26])([CH3:24])[CH3:23])[Br:17])([CH3:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 68509CumylamineHCID 20570578HCID 20570578, compound

Product 1

HCID 12760502HCID 12760502, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Into a 200 ml four-necked flask, there were charged benzene (100 ml), α,α-dimethylbenzylamine (9 g) and triethylamine (7.4 g), and α-bromo-tert-amylacetyl chloride (15.5 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. After the benzene layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was recrystallized from ethanol to give 15.8 g of N-(α,α-dimethylbenzyl)-α-bromo-tert-amylacetamide. M.P., 136°-137° 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 materialAfter the 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-9d771b842fc74060800857aeb3177cdf
Source dataset
uspto-grants-1981_09
Patent number
US04288244

Reaction notes

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