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

HRID 379987Notes

Reaction equation

HRID 379987 reaction equation
[CH3:1][NH2:2].[Br:3][C:4]1C=C[C:7](CC(O)=O)=[CH:6][CH:5]=1.[O:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1>CN(C)C1C=CN=CC=1.ClCCl>[Br:3][C:4]1[CH:15]=[C:16]([CH2:17][C:18]([NH:2][CH3:1])=[O:14])[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 74654Benzeneacetic acid, 4-bromo-

Product 1

HCID 186685292-(3-bromophenyl)-N-methylacetamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide 4-hydrochloride (8.88 g), 4-dimethylaminopyridine (5.67 g) and a 2M solution of methylamine in tetrahydrofuran (23 ml) were added to a solution of 4-bromophenylacetic acid (5.0 g) in dichloromethane (100 ml). The mixture was stirred overnight at room temperature. The reaction mixture was washed with 2M hydrochloric acid (3×100 ml), the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated. The sub-title compound was obtained as a solid (4.74 g) after recrystallisation from 1% hexane in ethyl acetate.

Workup

  1. washThe reaction mixture was washed with 2M hydrochloric acid (3×100 ml)
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4c8cb9574d864fdba5367adc7c7b4777
Source dataset
uspto-grants-2001_10
Patent number
US06300352B1

Reaction notes

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