Methylamine → 2-(2-Bromophenyl)-N-methylacetamide

HRID 380015Notes

Reaction equation

HRID 380015 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=O.CN.Cl.[CH3:15][N:16](C)CCCN=C=NCC>ClCCl.CN(C)C1C=CN=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([NH:16][CH3:15])=[O:11]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 877542-Bromophenylacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 183675232-(2-Bromophenyl)-N-methylacetamideYield 89.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromophenyl acetic acid (2.15 g) in dichloromethane (100 ml) was added methylamine (2M solution in tetrahydrofuran, 6 ml), 4-dimethylaminopyridine (1.32 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.055 g). The mixture was left to stir at room temperature for 16 hours, after which the organic portion was washed with 2M aqueous hydrogen chloride, dried over magnesium sulfate and filtered. The filtrate was concentrated to give a solid (2.04 g)

Workup

  1. waitThe mixture was left
  2. washafter which the organic portion was washed with 2M aqueous hydrogen chloride
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d64f05883aa241c192be766048f49826
Source dataset
uspto-grants-2001_10
Patent number
US06300352B1

Reaction notes

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