2,6-Dimethylaniline → N-(2,6-dimethylphenyl)-2-methoxyacetamide

HRID 1156833Notes

Reaction equation

HRID 1156833 reaction equation
[CH3:1][O:2][CH2:3][C:4](Cl)=[O:5].[CH3:7][C:8]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:9]=1[NH2:10].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:7][C:8]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:9]=1[NH:10][C:4](=[O:5])[CH2:3][O:2][CH3:1]

Participants

5

Reactant 3

HCID 68962,6-DimethylanilineHCID 8471TriethylamineHCID 96623Methoxyacetyl chloride

Product 1

HCID 10878014N-(2,6-dimethylphenyl)-2-methoxyacetamideYield 57%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

55 g (0.5 mol) of methoxyacetyl chloride were added dropwise to a solution of 61 g (0.5 mol) of 2,6-dimethylaniline and 50.5 g (0.5 mol) of triethylamine in 250 ml of toluene at 5° to 15° C., while stirring and cooling. The mixture was subsequently stirred at 20° C. for 2 hours, filtered and concentrated and the residue was taken up in water. The aqueous mixture was extracted with methylene chloride and the extract was dried over sodium sulphate and concentrated by distilling off the solvent. The residue was distilled under a high vacuum. 55 g (57% of theory) of 2,6-dimethyl-N-methoxyacetyl-aniline of boiling point 122°-132° C./0.1 mm Hg and of melting point 61°-63° C. were obtained. ##STR177##

Workup

  1. temperaturecooling
  2. stirringThe mixture was subsequently stirred at 20° C. for 2 hours
  3. filtrationfiltered
  4. concentrationconcentrated
  5. extractionThe aqueous mixture was extracted with methylene chloride
  6. dry with materialthe extract was dried over sodium sulphate
  7. concentrationconcentrated
  8. distillationby distilling off the solvent
  9. distillationThe residue was distilled under a high vacuum

Sources & evidence

ORD record
ord-8637958b54ba4c4181c22cb21766b6b4
Source dataset
uspto-grants-1982_06
Patent number
US04337268

Reaction notes

Loading…