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

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: According to the process described in the HU-PS 202,481, after acylating 2,6-dimethylaniline with methoxyacetic acid, the N-methoxyacetyl-2,6-dimethylaniline obtained is heated together with a twofold excess of methyl DL-α-bromopropionate to 120° C., and after adding sodium methoxide in small portions to the reaction mixture obtained, the alkylation is carried out at 140° C.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 30 g (0.155 mol) of 2,6-dimethyl-N-methoxyacetylaniline and 0.3 g of triethyl-benzyl-ammonium chloride were dissolved in a two-phase system mixture of 100 ml of 50% strength sodium hydroxide solution and 250 ml of toluene, and 19 g (0.016 mol) of propargyl bromide were added, whilst stirring vigorously. The mixture was stirred for 4 hours and the toluene phase was separated off, washed several times with water, dried over sodium sulphate and concentrated by distilling off the solvent under a waterpump vacuum. The residue was distilled under a high vacuum. 26.5 g (74% of theory) of 2,6-dimethyl-N-methoxyacetyl-N-propargyl-aniline of boiling point 140°/0.4 mm Hg and of melting point 49°-51° C. were obtained. ##STR178## were added The mixture was stirred for 4 hours the toluene phase was separated off washed several times with water dried over sodium sulphate concentrated by distilling off the solvent under a waterpump vacuum The residue was distilled under a high vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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## cooling The mixture was subsequently stirred at 20° C. for 2 hours filtered concentrated The aqueous mixture was extracted with methylene chloride the extract was dried over sodium sulphate concentrated by distilling off the solvent The residue was distilled under a high vacuum