Ammonia → HCID 67930020, compound

HRID 358723Notes

Reaction equation

HRID 358723 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([NH:7][C:8](=[O:10])[CH3:9])=[CH:5][C:4]=1[CH3:13].[H-].[Na+].I[CH3:17].N>O1CCCC1>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([N:7]([CH3:17])[C:8](=[O:10])[CH3:9])=[CH:5][C:4]=1[CH3:13]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 4004288HCID 4004288, compound

Product 1

HCID 67930020HCID 67930020, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4'-methoxy-3'-methylacetanilide (71g) in dry tetrahydrofuran (350 ml) was added over 45 minutes to a stirred suspension of sodium hydride (19 g of a 50% dispersion in mineral oil) in dry tetrahydrofuran (250 ml) under nitrogen. The stirred mixture was heated under reflux for 10 minutes, then cooled to 0 to 5° and iodomethane (25 ml) added dropwise over 10 minutes. After the mixture was stirred and heated under reflux for a further 2 hours, the mixture was cooled to ambient temperature and industrial methylated spirit (50 ml) followed by aqueous ammonia (specific gravity 0.88, 50 ml) were added. After 30 minutes, solvent was removed by evaporation, water (500 ml) added to the residue and the mixture extracted with ethyl acetate (3×300 ml). The combined extracts were washed with aqueous sodium metabisulphite (10% w/w, 2×300 ml), dried over magnesium sulphate, and the solvent removed by evaporation. The residue was triturated with petroleum ether (b.p. 40°-60° ) and the solid collected by filtration to give the novel compound 4'-methoxy-3'-methyl-N-methylacetanilide, m.p. 65°-66°.

Workup

  1. temperatureThe stirred mixture was heated
  2. temperatureunder reflux for 10 minutes
  3. temperaturecooled to 0 to 5°
  4. temperatureheated
  5. temperatureunder reflux for a further 2 hours
  6. additionwere added
  7. customsolvent was removed by evaporation, water (500 ml)
  8. additionadded to the residue
  9. extractionthe mixture extracted with ethyl acetate (3×300 ml)
  10. washThe combined extracts were washed with aqueous sodium metabisulphite (10% w/w, 2×300 ml)
  11. dry with materialdried over magnesium sulphate
  12. customthe solvent removed by evaporation
  13. customThe residue was triturated with petroleum ether (b.p. 40°-60° )
  14. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-e871b12fb7b34d6483a07f7aba9a3ba5
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

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