Propargyl bromide → N-(2-Methoxyacetyl)-N-(2-propynyl)-2,6-dimethylbenzenamine

HRID 1156834Notes

Reaction equation

HRID 1156834 reaction equation
[CH3:1][C:2]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:3]=1[NH:4][C:5](=[O:9])[CH2:6][O:7][CH3:8].[CH2:15](Br)[C:16]#[CH:17]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.[OH-].[Na+].C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:3]=1[N:4]([C:5](=[O:9])[CH2:6][O:7][CH3:8])[CH2:17][C:16]#[CH:15]

Participants

6

Reactant 2

HCID 7842Propargyl bromideHCID 10878014N-(2,6-dimethylphenyl)-2-methoxyacetamide

Product 1

HCID 13150482N-(2-Methoxyacetyl)-N-(2-propynyl)-2,6-dimethylbenzenamineYield 716.1%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolventHCID 14798Sodium HydroxideSolvent

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##

Workup

  1. additionwere added
  2. stirringThe mixture was stirred for 4 hours
  3. customthe toluene phase was separated off
  4. washwashed several times with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. distillationby distilling off the solvent under a waterpump vacuum
  8. distillationThe residue was distilled under a high vacuum

Sources & evidence

ORD record
ord-069a200d8a434c888669e929a4df7110
Source dataset
uspto-grants-1982_06
Patent number
US04337268

Reaction notes

Loading…