2,4-Dimethylaniline → 2-bromo-N-(2,4-dimethylphenyl)acetamide

HRID 1266516Notes

Reaction equation

HRID 1266516 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:10]=1[NH2:11].[Br:17][CH2:18][C:19](Br)=[O:20]>C(Cl)Cl>[Br:17][CH2:18][C:19]([NH:11][C:10]1[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:9]=1[CH3:8])=[O:20]

Participants

5

Reactant 3

HCID 72502,4-DimethylanilineHCID 8471TriethylamineHCID 61147Bromoacetyl bromide

Product 1

HCID 113339582-bromo-N-(2,4-dimethylphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

117 g of triethylamine and 140 g of 2,4-dimethylaniline are dissolved in 21 of methylene chloride, and a solution of 233 g of alpha-bromoacetyl bromide in 400 ml of methylene chloride is added with ice-cooling, at at most 15° C., within 30 min. After a reaction time of 30 min, the precipitate is filtered off with suction, the residue is dissolved in 3 l of methylene chloride and combined with the filtrate and washed twice with 2 l of water and 2 l of sat. sodium chloride solution. The mixture is dried over sodium sulphate, filtered off with suction and concentrated, and the residue is recrystallized from ethanol. This gives 193 g of the title compound.

Workup

  1. temperaturecooling, at at most 15° C., within 30 min
  2. filtrationAfter a reaction time of 30 min, the precipitate is filtered off with suction
  3. dissolutionthe residue is dissolved in 3 l of methylene chloride
  4. washwashed twice with 2 l of water and 2 l of sat. sodium chloride solution
  5. dry with materialThe mixture is dried over sodium sulphate
  6. filtrationfiltered off with suction
  7. concentrationconcentrated
  8. customthe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-99459278ce044cd9b126fbb840a4a04c
Source dataset
uspto-grants-2003_04
Patent number
US06548538B2

Reaction notes

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