Methylamine → 2-(3-bromophenyl)-N-methylacetamide

HRID 1059215Notes

Reaction equation

HRID 1059215 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:6][CH:7]=1.CN.Cl.[CH3:15][N:16](C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>C1COCC1.CN(C=O)C.C(OCC)(=O)C.C(N(CC)CC)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([NH:16][CH3:15])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 6329MethylamineHCID 74653(3-Bromophenyl)acetic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 186685292-(3-bromophenyl)-N-methylacetamideYield 40.6%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-bromophenylacetic acid (3.02 g), a solution (2.0 M; 8.5 ml) of methylamine in THF, 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (3.20 g), 1-hydroxybenzotriazole (2.60 g) and triethylamine (2.3 ml) was stirred in DMF (30 ml) at room temperature for 24 h. The reaction mixture was diluted with ethyl acetate, washed successively with water, 1N aqueous sodium hydroxide solution, 1N hydrochloric acid, aqueous sodium hydrogen carbonate and brine, dried (magnesium sulfate) and concentrated under reduced pressure. The residue was purified by silica gel chomatography (eluent; ethyl acetate). Recrystallization from hexane-ethyl acetate gave the title compound (1.30 g) as colorless prism crystals.

Workup

  1. washwashed successively with water, 1N aqueous sodium hydroxide solution, 1N hydrochloric acid, aqueous sodium hydrogen carbonate and brine
  2. dry with materialdried (magnesium sulfate)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chomatography (eluent; ethyl acetate)
  5. customRecrystallization from hexane-ethyl acetate

Sources & evidence

ORD record
ord-c8d2be4b8a4f462eade6f5e359f8af53
Source dataset
uspto-grants-2003_02
Patent number
US06518257B1

Reaction notes

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