Benzene → Bromobutide

HRID 1577467

Reaction equation

HRID 1577467 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]([CH3:25])([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]([CH3:25])([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 108676212-Bromo-3,3-dimethylbutanoyl chloride

Product 1

HCID 53079BromobutideYield 73.6%

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-butylacetyl chloride (14.5 g) was dropwise added thereto while stirring at room temperature. Stirring was continued for 3 hours. 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 obtained residue was recrystallized from ethanol to give 15.3 g of N-(α,α-dimethylbenzyl)-α-bromo-tert-butylacetamide. M.P., 182°-183° C.

Workup

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

Sources & evidence

ORD record
ord-6533c47c46e047fead1c18a1f7f5fbfb
Source dataset
uspto-grants-1981_09
Patent number
US04288244

Linked notes

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