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

HRID 465673Notes

Reaction equation

HRID 465673 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[CH:6]([C:9]1[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]([CH3:18])[CH3:17])[C:10]=1[NH2:11])([CH3:8])[CH3:7].C([O-])(=O)C.[Na+]>CC(C)=O.O>[CH3:18][CH:16]([C:12]1[CH:13]=[CH:14][CH:15]=[C:9]([CH:6]([CH3:8])[CH3:7])[C:10]=1[NH:11][C:3](=[O:4])[CH2:2][Br:1])[CH3:17]

Participants

6

Reactant 3

HCID 32484DiisopropylanilineHCID 61147Bromoacetyl bromideHCID 517045Sodium Acetate

Product 1

HCID 12149064Acetamide, N-[2,6-bis(1-methylethyl)phenyl]-2-bromo-Yield 86.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

Bromoacetyl bromide (17.0 g, 84.6 mmol) was added dropwise to a well-stirred ice cold solution of 2,6-diisopropylaniline (10.0 g, 56.4 mmol) in acetone (25 mL) and water (25 mL) containing sodium acetate (15.3 g, 112.8 mmol). The reaction mixture was stirred at room temperature for an hour and then diluted with water (100 mL). The product was filtered and washed with cold water, saturated sodium, bicarbonate, again with water, and finally with hexane. It was dried in a vacuum at 40° C. to yield 14.5 g (86%) of title compound as a white solid 1H NMR was consistent with the title compound.

Workup

  1. filtrationThe product was filtered
  2. washwashed with cold water, saturated sodium, bicarbonate, again with water
  3. customIt was dried in a vacuum at 40° C.

Sources & evidence

ORD record
ord-7e395e075a70406ea2ca80314162b8f8
Source dataset
uspto-grants-1992_10
Patent number
US05153226

Reaction notes

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