Methylamine → 3-(chloromethyl)-N-methylbenzamide

HRID 483368Notes

Reaction equation

HRID 483368 reaction equation
[Cl:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].CN.[CH2:14]([N:16](CC)CC)C>C(Cl)Cl>[Cl:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH:16][CH3:14])=[O:7]

Participants

5

Reactant 3

HCID 6329Methylamine2×HCID 8471TriethylamineHCID 27333243-(Chloromethyl)benzoyl chloride

Product 1

HCID 226602083-(chloromethyl)-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-chloromethylbenzoyl chloride (7.4 g, Aldrich) in DCM (35 ml) was added dropwise at 0° C. over 30 minutes to a stirred mixture of 30% aqu. methylamine (4.5 ml) and triethylamine (3.6 g) in DCM (50 ml). When addition was complete, the mixture was allowed to warm to room temperature over 1 hour with stirring. Further methylamine (0.5 ml) was added and the mixture stirred for a further 10 minutes, then washed with water, 1N aqu. HCl, 1N aqu. NaOH and brine, dried over MgSO4 and evaporated in vacuo to give the desired product as a colourless oil which solidified to a white solid on standing.

Workup

  1. additionWhen addition
  2. stirringthe mixture stirred for a further 10 minutes
  3. washwashed with water, 1N aqu
  4. dry with materialNaOH and brine, dried over MgSO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-fdf113d3b5e94577a2f85455806ce590
Source dataset
uspto-grants-1993_07
Patent number
US05225431

Reaction notes

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