Dimethylamine → 3-(chloromethyl)-N,N-dimethylbenzamide

HRID 750515Notes

Reaction equation

HRID 750515 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].C[CH2:13][N:14](CC)[CH2:15]C.CNC.O>C1COCC1>[Cl:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([N:14]([CH3:15])[CH3:13])=[O:7]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 962WaterHCID 8471TriethylamineHCID 27333243-(Chloromethyl)benzoyl chloride

Product 1

HCID 218746043-(chloromethyl)-N,N-dimethylbenzamideYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-(chloromethyl)benzoyl chloride (426 μL, 3 mmol) and Et3N (626 μL, 4.5 mmol) in THF (5 mL) was treated with dimethylamine (1.5 mL, 2-M in THF, 3 mmol), stirred at room temperature for 1 h, poured into water, extracted with EtOAc, dried (MgSO4) and concentrated in vacuo to give the title compound (580 mg, 98%) as a colourless oil; NMR δH (400 MHz, CDCl3) 7.46-7.34 (4H, m), 4.59 (2H, s), 3.11 (3H, s) and 2.98 (3H, s); Anal. Calcd for C12H12N6O2.0.2H2O: C, 49.38; H, 4.28, N, 28.79. Found: C, 49.25; H, 4.09; N, 28.47.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bb05ce0a48bc411cbe0f1d6a2a45e5df
Source dataset
uspto-grants-2008_07
Patent number
US07405219B2

Reaction notes

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