Sodium Chloride → alpha-chloro-N-[2-methylpropoxymethyl]-N-[2,6-dimethoxyphenyl]acetamide

HRID 1577463Notes

Reaction equation

HRID 1577463 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)[CH:20](C)[CH3:21].CS(O)(=O)=O.[Cl-].[Na+]>C1(C)C(C)=CC=CC=1>[Cl:1][CH2:2][C:3]([N:5]([CH2:16][O:17][CH2:18][CH:20]([CH3:21])[CH3:19])[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

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6395Methanesulfonic AcidHCID 6560IsobutanolHCID 20554723alpha-chloro-N-(methoxymethyl)-N-(2,6-dimethoxyphenyl)acetamide

Product 1

HCID 20570573alpha-chloro-N-[2-methylpropoxymethyl]-N-[2,6-dimethoxyphenyl]acetamideYield 88%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture containing alpha-chloro-N-[methoxymethyl]-N-[2,6-dimethoxyphenyl]acetamide (4.9 g; 0.018 mole), 20 ml. of isobutanol and 0.2 ml. of methanesulfonic acid in 150 ml. of xylene was heated at reflux temperature for 2 hours under a soxhlet extractor containing 20 g. of activated 3A molecular sieves. The reaction mixture was then cooled to 26° C. after which time a 2.5% sodium chloride solution was added to the reaction mixture. The layers were separated and the organic layer was dried, filtered and concentrated to yield a yellow solid. The yellow solid was recrystallized from heptane to yield alpha-chloro-N-[2-methylpropoxymethyl]-N-[2,6-dimethoxyphenyl]acetamide (5.0 g; 88% yield) as white crystals having a melting point of 107°-110° C. and the following analysis:

Workup

  1. temperatureat reflux temperature for 2 hours under a soxhlet extractor
  2. additioncontaining 20 g
  3. additionwas added to the reaction mixture
  4. customThe layers were separated
  5. customthe organic layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield a yellow solid
  9. customThe yellow solid was recrystallized from heptane

Sources & evidence

ORD record
ord-1b0063abbe6b41caae6aa15882d09d7e
Source dataset
uspto-grants-1981_09
Patent number
US04288242

Reaction notes

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