Methanol → HCID 15016279, compound

HRID 2106598Notes

Reaction equation

HRID 2106598 reaction equation
[C:1]([CH:4]([O:6][C:7]1[N:11]=[CH:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:8]=1)[CH3:5])([OH:3])=O.[Na].[CH3:19][OH:20]>>[CH2:19]([O:20][C:1]([CH:4]([O:6][C:7]1[N:11]=[CH:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:8]=1)[CH3:5])=[O:3])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 5360545SodiumHCID 15016244HCID 15016244, compound

Product 1

HCID 15016279HCID 15016279, compound

Procedure

A 5.5 g portion of the compound of Example 22 was added to 50 ml of methanol containing 0.54 g of sodium, and the mixture was heated briefly to reflux. It was then cooled and the solvent was removed under vacuum. To it was added 75 ml of toluene, 2.6 ml of benzyl chloride and 2.3 g of triethylamine, and the mixture was heated under reflux for 22 hours. It was then cooled, poured over ice-water, and extracted with ethyl acetate. The extract was washed with water and with saturated brine, and was dried with sodium sulfate and phase separation paper. It was then evaporated under vacuum, and the residue was recrystallized from ethanol-water to obtain 2.5 g of the desired product, m.p. 78°-80°.

Workup

  1. temperaturethe mixture was heated briefly
  2. temperatureto reflux
  3. temperatureIt was then cooled
  4. customthe solvent was removed under vacuum
  5. additionTo it was added 75 ml of toluene, 2.6 ml of benzyl chloride and 2.3 g of triethylamine
  6. temperaturethe mixture was heated
  7. temperatureunder reflux for 22 hours
  8. temperatureIt was then cooled
  9. additionpoured over ice-water
  10. extractionextracted with ethyl acetate
  11. washThe extract was washed with water and with saturated brine
  12. dry with materialwas dried with sodium sulfate and phase separation paper
  13. customIt was then evaporated under vacuum
  14. customthe residue was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-b6720745f7f54c4eb417990d5edbbb2c
Source dataset
uspto-grants-1990_06
Patent number
US04931083

Reaction notes

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