Triethylamine → Acetamide, 2-bromo-N-(2,3-dimethylphenyl)-N-methyl-

HRID 581183Notes

Reaction equation

HRID 581183 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[CH3:10].C(N(CC)CC)C.[Br:18][CH2:19][C:20](Br)=[O:21]>ClCCl>[CH3:1][N:2]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[CH3:10])[C:20](=[O:21])[CH2:19][Br:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 10909621HCID 10909621, compound

Product 1

HCID 10682477Acetamide, 2-bromo-N-(2,3-dimethylphenyl)-N-methyl-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-Methyl-2,3-dimethylaniline S14 (4.6 g) and triethylamine (5.0 ml) were dissolved in dichloromethane (50 ml). 2-Bromoacetyl bromide (3.0 ml) in dichloromethane (30 ml) was added to the resulting solution under ice cooling and the solution was stirred for 2 hours at room temperature. The reaction mixture was washed successively with 1N HCl, water and brine, then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, obtaining 8.4 g of the title compound as an oily substance.

Workup

  1. washThe reaction mixture was washed successively with 1N HCl, water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-2f8c2c291fdf4a5fb355dd6e0dd2a05c
Source dataset
uspto-grants-1999_07
Patent number
US05919824

Reaction notes

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