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

HRID 379979Notes

Reaction equation

HRID 379979 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.[CH3:14][N:15](C1C=CC=CN=1)C.Cl.CN(C)CCCN=C=NCC>ClCCl.O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([NH:15][CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 218852-DimethylaminopyridineHCID 74653(3-Bromophenyl)acetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 186685292-(3-bromophenyl)-N-methylacetamideYield 81.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-bromophenyl acetic acid (2.15 g), a tetrahydrofuran solution of methyl amine (6 ml, 2M), dimethylaminopyridine (1.32 g), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.06 g) in dichloromethane was stirred at room temperature for 16 hrs. The organic solution was washed thrice with 2M hydrochloric acid solution, dried over magnesium sulphate, filtered and evaporated to afford a solid (1.86 g).

Workup

  1. washThe organic solution was washed thrice with 2M hydrochloric acid solution
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-e45cf6e853384e42a1d9cddacc75aea5
Source dataset
uspto-grants-2001_10
Patent number
US06300352B1

Reaction notes

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