1-Butanol → alpha-chloro-N-(butoxymethyl)-N-(2,6-dimethoxyphenyl)acetamide

HRID 1577461Notes

Reaction equation

[Cl:1][CH2:2][C:3]([N:5]([CH2:16][O:17][CH3:18])[C:6]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=1[O:14][CH3:15])=[O:4].[CH2:19](O)[CH2:20][CH2:21]C.CS(O)(=O)=O>C1(C)C=CC=CC=1>[Cl:1][CH2:2][C:3]([N:5]([CH2:16][O:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:6]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=1[O:14][CH3:15])=[O:4]

Participants

Conditions

Temperature: 26 °C

Procedure

A mixture containing alpha-chloro-N-[methoxymethyl]-N-[2,6-dimethoxyphenyl]acetamide (4.0 g; 0.015 mole), 150 ml. of n-butanol and 0.2 ml. of methylsulfonic acid in 150 ml. of toluene was refluxed for 7 hours in a soxhlet extractor containing 22 g. of activated 3A molecular sieves. The reaction mixture was allowed to cool to 26° C. and was then washed with a 5% sodium carbonate solution. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuo to yield a dark oil. The dark oil was distilled at 170° C. (0.05 mm) to yield alpha-chloro-N-(butoxymethyl)-N-(2,6-dimethoxyphenyl)acetamide (2.7 g; 57% yield) as a clear colorless oil having a boiling point of 170° C. at 0.05 mmHg and the following analysis:

Workup

additioncontaining 22 g
washwas then washed with a 5% sodium carbonate solution
customThe organic layer was separated
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customto yield a dark oil
distillationThe dark oil was distilled at 170° C. (0.05 mm)

Sources & evidence

ORD record: ord-81e0d0e43e4845eaa521f3fd92993352
Source dataset: uspto-grants-1981_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04288242

Reaction notes

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