Methoxyacetyl chloride → N-(2-Methoxyacetyl)-N-(2-propynyl)-2,6-dimethylbenzenamine

HRID 1758259Notes

Reaction equation

HRID 1758259 reaction equation
[CH2:1]([NH:4][C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:12])[C:2]#[CH:3].[CH3:13][O:14][CH2:15][C:16](Cl)=[O:17]>C1(C)C=CC=CC=1>[CH3:13][O:14][CH2:15][C:16]([N:4]([CH2:1][C:2]#[CH:3])[C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:12])=[O:17]

Participants

4

Reactant 2

HCID 96623Methoxyacetyl chlorideHCID 2997052,6-dimethyl-N-prop-2-ynyl-aniline

Product 1

HCID 13150482N-(2-Methoxyacetyl)-N-(2-propynyl)-2,6-dimethylbenzenamineYield 55.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3.18 g (0.02 mole) of N-(2-propynyl)-2,6-dimethylbenzenamine, 2.4 g (0.022 mole) of methoxyacetyl chloride and 6 g of 4A molecular sieves in 100 ml of toluene is stirred at 60° overnight under a nitrogen atmosphere. The reaction mixture is cooled to room temperature and then filtered. The filtrate is combined with 200 ml of ether and washed with water, saturated sodium chloride solution, and dried over sodium sulfate. The drying agent is filtered and the solvent is evaporated under vacuum to give an orange-red oily material which is further purified by column chromatography (silica gel) using 20/80 ethyl acetate-n-hexane as solvent to give 2.57 g of pure product.

Workup

  1. filtrationfiltered
  2. washwashed with water, saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationThe drying agent is filtered
  5. customthe solvent is evaporated under vacuum
  6. customto give an orange-red oily material which
  7. customis further purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-d8dd67c65dcc41769e912161274d42f8
Source dataset
uspto-grants-1983_02
Patent number
US04372972

Reaction notes

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