Diisopropylaniline → Acetamide, N-[2,6-bis(1-methylethyl)phenyl]-2-bromo-

HRID 247836

Reaction equation

HRID 247836 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH3:13])[CH3:12])[C:5]=1[NH2:6])([CH3:3])[CH3:2].O.O.O.C([O-])(=O)C.[Na+].[Br:22][CH2:23][C:24](Br)=[O:25]>CC(C)=O.O>[CH3:12][CH:11]([C:7]1[CH:8]=[CH:9][CH:10]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]=1[NH:6][C:24](=[O:25])[CH2:23][Br:22])[CH3:13]

Participants

6

Reactant 3

HCID 32484DiisopropylanilineHCID 61147Bromoacetyl bromideHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 12149064Acetamide, N-[2,6-bis(1-methylethyl)phenyl]-2-bromo-Yield 86.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

To a well-stirred ice-cooled mixture of 2,6-diisopropylaniline (10.0 g, 0.056 mol) in acetone (25 mL) and water (25 mL) and sodium acetate trihydrate (15.3 g, 0.112 mol), bromoacetyl bromide (17.0 g, 0.084 mol) is added dropwise. The reaction mixture is allowed to warm to room temperature and stirred for 1 hour. The reaction mixture is diluted with water (100 mL), the product filtered, washed with cold water, sodium bicarbonate solution, water, and finally with hexane. The product is dried in a vacuum at 40° C. to afford 14.5 g of the title compound as a white solid; mp I70° C.

Workup

  1. additionis added dropwise
  2. filtrationthe product filtered
  3. washwashed with cold water, sodium bicarbonate solution, water
  4. customThe product is dried in a vacuum at 40° C.

Sources & evidence

ORD record
ord-d5a959fffbcc4c339707cebc8fa87a56
Source dataset
uspto-grants-1993_05
Patent number
US05208224

Linked notes

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