Triethylamine → N-(3,5-dimethyl-4-methoxyphenyl)-2-methoxyacetamide

HRID 1534860Notes

Reaction equation

HRID 1534860 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([CH3:11])[C:8]=1[O:9][CH3:10])[NH2:5].C(N(CC)CC)C.[CH3:19][O:20][CH2:21][C:22](Cl)=[O:23]>ClCCl>[CH3:1][C:2]1[CH:3]=[C:4]([NH:5][C:22](=[O:23])[CH2:21][O:20][CH3:19])[CH:6]=[C:7]([CH3:11])[C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 96623Methoxyacetyl chlorideHCID 41660974-Methoxy-3,5-dimethylaniline

Product 1

HCID 19908414N-(3,5-dimethyl-4-methoxyphenyl)-2-methoxyacetamideYield 90.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5.00 g (33 mmol) of 3,5-dimethyl-4-methoxyaniline and 7.1 ml of triethylamine in 50 ml of dichloromethane was dropwise added a solution of 4.31 g (40 mmol) of methoxyacetylchloride in 20 ml of dichloromethane under chilling with ice for a period of 30 min. The resulting mixture was stirred for 30 min. at room temperature. The reaction mixture was washed sequentially with 5 aqueous sodium carbonate and 3 N hydrochloric acid, and then dried over anhydrous sodium sulfate. Dichloromethane was distilled off. The residue was crystallized from ether hexane to obtain 6.70 g of the desired compound as a white crystal. (Yield: 90.7 %)

Workup

  1. temperatureunder chilling with ice for a period of 30 min
  2. washThe reaction mixture was washed sequentially with 5 aqueous sodium carbonate and 3 N hydrochloric acid
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationDichloromethane was distilled off
  5. customThe residue was crystallized from ether hexane

Sources & evidence

ORD record
ord-a265c314a8694ed999ac088f0853a26e
Source dataset
uspto-grants-1992_02
Patent number
US05091403

Reaction notes

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