Benzene → N-(1-phenylcyclopropyl)-alpha-bromo-tert-butylacetamide

HRID 1577472Notes

Reaction equation

HRID 1577472 reaction equation
C1C=CC=CC=1.[C:7]1([C:13]2([NH2:16])[CH2:15][CH2:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Br:17][CH:18]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:19](Cl)=[O:20]>C(N(CC)CC)C>[C:7]1([C:13]2([NH:16][C:19](=[O:20])[CH:18]([C:22]([CH3:25])([CH3:24])[CH3:23])[Br:17])[CH2:15][CH2:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 1945491-Phenyl-cyclopropylamineHCID 108676212-Bromo-3,3-dimethylbutanoyl chloride

Product 1

HCID 12760535N-(1-phenylcyclopropyl)-alpha-bromo-tert-butylacetamideYield 71.4%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Into a 200 ml four-necked flask, there were charged benzene (100 ml), 1-phenylcyclopropylamine (8.9 g) and triethylamine (7.4 g), and α-bromo-tert-butylacetyl chloride (14.5 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. The benzene layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was recrystallized from ethanol to give 14.8 g of N-(1-phenylcyclopropyl)-α-bromo-tert-butylacetamide. M.P., 161°-162.5° 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 obtained residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-a7189525640c4b379108d7190376d22a
Source dataset
uspto-grants-1981_09
Patent number
US04288244

Reaction notes

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