1-Propanol → alpha-chloro-N-[propoxymethyl]-N-[2,6-dimethoxyphenyl]acetamide

HRID 1577462Notes

Reaction equation

HRID 1577462 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]C.CS(O)(=O)=O>CCOCC>[Cl:1][CH2:2][C:3]([N:5]([CH2:16][O:17][CH2:18][CH2:19][CH3:20])[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

5

Reactant 3

HCID 10311-PropanolHCID 6395Methanesulfonic AcidHCID 20554723alpha-chloro-N-(methoxymethyl)-N-(2,6-dimethoxyphenyl)acetamide

Product 1

HCID 12953502alpha-chloro-N-[propoxymethyl]-N-[2,6-dimethoxyphenyl]acetamideYield 68%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture containing alpha-chloro-N-[methoxymethyl]-N-[2,6-dimethoxyphenyl]acetamide (4.4 g; 0.0161 mole), 150 ml. of n-propanol and 0.2 ml. of methanesulfonic acid was heated at reflux temperature for 9 hours in a soxhlet extractor containing 22 g. of activated 3A molecular sieves. The reaction mixture was allowed to stand at 26° C. for 16 hours and was then concentrated in vacuo yielding a crude product. The crude product was taken up in ether and the ether solution was washed with a 5% sodium carbonate solution. The layers were separated and the organic ether layer was dried over magnesium sulfate, filtered and concentrated in vacuo to yield a white solid. The white solid was recrystallized from hexane to yield alpha-chloro-N-[propoxymethyl]-N-[2,6-dimethoxyphenyl]acetamide (3.3 g; 68% yield) as a white solid having a melting point of 83°-85° C. and the following analysis:

Workup

  1. temperatureat reflux temperature for 9 hours in a soxhlet extractor
  2. additioncontaining 22 g
  3. concentrationwas then concentrated in vacuo
  4. customyielding a crude product
  5. washthe ether solution was washed with a 5% sodium carbonate solution
  6. customThe layers were separated
  7. dry with materialthe organic ether layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto yield a white solid
  11. customThe white solid was recrystallized from hexane

Sources & evidence

ORD record
ord-ec0b6d86584c496391f06e225d9a2684
Source dataset
uspto-grants-1981_09
Patent number
US04288242

Reaction notes

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