Sodium Hydroxide → HCID 53795900, compound

HRID 1105631Notes

Reaction equation

HRID 1105631 reaction equation
[OH-].[Na+].C([NH:6][CH:7]([CH3:23])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH3:22])=[CH:16][C:17]([O:19][CH2:20]C)=[O:18])=[CH:11][CH:10]=1)(=O)C>O>[C:17]([CH:16]=[C:15]([C:12]1[CH:11]=[CH:10][C:9]([CH2:8][CH:7]([CH3:23])[NH2:6])=[CH:14][CH:13]=1)[CH3:22])([O:19][CH3:20])=[O:18]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53710554HCID 53710554, compound

Product 1

HCID 53795900HCID 53795900, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of sodium hydroxide (6 g) in water (30 ml) was added to N-acetyl-2-{4-(2-carboethoxy-1-methylethenyl)phenyl}-1-methylethanamine (8.5 g) and the mixture stirred and heated under reflux for 8 hrs. The solution was cooled and evaporated to dryness. The residue was dissolved in methanol (30 ml) and made acid by addition of conc. HCl. The precipitated sodium chloride was removed by filtration, and the methanol solution dried over molecular sieves overnight. This solution was then added to a solution of thionyl chloride (8 ml) in dry methanol (10 ml) kept at -70° C. by Dry Ice/acetone. After warming to ambient temperature, the solution was stirred and heated under reflux for 1 hour. The solution was cooled, filtered and evaporated, the residue shaken with an aqueous solution of potassium carbonate and extracted with chloroform. The chloroform extract was dried (MgSO4) and evaporated to leave an oil, (2.8 g). τ(CDCl3) 8.9 (3H, d, J=8 Hz), 8.5 (2H, bs, exchangeable with D2O), 7.45 (3H, d, J=1.5 Hz). 7.2-7.4 (2H, m), 6.6-7.0 (1H, m), 6.3 (3H, s), 3.92 (1H, q, J=1.5 Hz), 2.5-3.0 (4H, m).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 8 hrs
  3. temperatureThe solution was cooled
  4. customevaporated to dryness
  5. dissolutionThe residue was dissolved in methanol (30 ml)
  6. additionby addition of conc. HCl
  7. customThe precipitated sodium chloride was removed by filtration
  8. dry with materialthe methanol solution dried over molecular sieves overnight
  9. additionThis solution was then added to a solution of thionyl chloride (8 ml) in dry methanol (10 ml)
  10. customkept at -70° C. by Dry Ice/acetone
  11. stirringthe solution was stirred
  12. temperatureheated
  13. temperatureunder reflux for 1 hour
  14. temperatureThe solution was cooled
  15. filtrationfiltered
  16. customevaporated
  17. stirringthe residue shaken with an aqueous solution of potassium carbonate
  18. extractionextracted with chloroform
  19. extractionThe chloroform extract
  20. dry with materialwas dried (MgSO4)
  21. customevaporated
  22. customto leave an oil, (2.8 g)

Sources & evidence

ORD record
ord-dd1795502da64aeea0a51bab6e9f5d5c
Source dataset
uspto-grants-1982_01
Patent number
US04309443

Reaction notes

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