1-Bromo-2-butanone → N-(3-isopropylphenyl)-N-(2-oxobutyl)-3-chlorophenylacetamide

HRID 486295Notes

Reaction equation

HRID 486295 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[CH2:20]([C:22]([CH2:24]Br)=[O:23])[CH3:21].[Cl:26][C:27]1[CH:28]=[C:29]([CH2:33][C:34](Cl)=[O:35])[CH:30]=[CH:31][CH:32]=1>C1(C)C=CC=CC=1.O.N1C=CC=CC=1>[CH:1]([C:4]1[CH:5]=[C:6]([N:7]([CH2:24][C:22](=[O:23])[CH2:20][CH3:21])[C:34](=[O:35])[CH2:33][C:29]2[CH:30]=[CH:31][CH:32]=[C:27]([Cl:26])[CH:28]=2)[CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 131561-Bromo-2-butanoneHCID 81531DiisopropylethylamineHCID 4586793-IsopropylanilineHCID 106552492-(3-chlorophenyl)acetyl Chloride

Product 1

HCID 11783283N-(3-isopropylphenyl)-N-(2-oxobutyl)-3-chlorophenylacetamideYield 93%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 1140TolueneSolvent

Procedure

200 g (1.48 mol) of m-isopropylaniline were dissolved in 600 ml of toluene, and 284 ml of diisopropylethylamine were then added thereto. The solution was heated to 45° C. under a nitrogen stream, and 245.8 g (1.63 mols) of bromomethyl ethyl ketone were added dropwise over 3 hours. After the temperature of the solution was returned to room temperature, 132 ml of pyridine were added thereto, and 308 g (1.63 mols) of m-chlorophenylacetyl chloride were then added dropwise thereto. The reaction mixture was poured into water, and the resultant organic layer was separated, washed with an aqueous saturated sodium bicarbonate solution and water in this order, and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 492.8 g of a crude product in an oily state (yield: 93.0%).

Workup

  1. additionwere added dropwise over 3 hours
  2. customwas returned to room temperature
  3. customthe resultant organic layer was separated
  4. washwashed with an aqueous saturated sodium bicarbonate solution and water in this order
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e394e961de704dcb969ddcf2e43f2d4a
Source dataset
uspto-grants-1994_03
Patent number
US05290949

Reaction notes

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