Triethylamine → HCID 12562460, compound

HRID 1657588Notes

Reaction equation

HRID 1657588 reaction equation
C([N:3](CC)CC)C.[CH2:8]([C:10]1[CH:20]=[CH:19][CH:18]=[CH:17][C:11]=1[CH:12]=CC(O)=O)[CH3:9].[CH2:21]([O:23]C(Cl)=O)[CH3:22].[N-]=[N+]=[N-].[Na+]>CC(C)=O.O>[CH2:8]([C:10]1[NH:3][C:21](=[O:23])[C:22]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:11][CH:12]=2)[CH3:9]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 4715295HCID 4715295, compound

Product 1

HCID 12562460HCID 12562460, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent3×HCID 962WaterSolvent

Procedure

88.3 g (0.87 mole) of triethylamine in 100 ml of absolute acetone were added dropwise to 128 g (0.73 mole) of 2-ethylcinnamic acid in 1200 ml of absolute acetone. The whole was stirred for 10 minutes and 94.6 g (0.87 mole) of chloroformic acid ethyl ester in 100 ml of absolute acetone were added dropwise with stirring. After 1 hour, a concentrated solution of 65 g (1 mole) of sodium azide in a small amount of water was added dropwise and stirring was continued for 30 minutes. The major part of the solvent was removed at room temperature under reduced pressure and the residue was poured onto ice. Extraction was effected with methylene chloride and the organic phase was washed with water and dried carefully over MgSC4. This solution of the acid azide was added dropwise into 350 ml of boiling diphenyl ether, during which time the methylene chloride was simultaneously distilled off. The whole was further heated for 1 hour under reflux and then the solvent was removed under reduced pressure. The residue was recrystallized from ethanol. M.p. 139° to140° C.

Workup

  1. stirringwith stirring
  2. waitAfter 1 hour
  3. stirringstirring
  4. waitwas continued for 30 minutes
  5. customThe major part of the solvent was removed at room temperature under reduced pressure
  6. additionthe residue was poured onto ice
  7. extractionExtraction
  8. washthe organic phase was washed with water
  9. dry with materialdried carefully over MgSC4
  10. additionThis solution of the acid azide was added dropwise into 350 ml of boiling diphenyl ether, during which time the methylene chloride
  11. distillationwas simultaneously distilled off
  12. temperatureThe whole was further heated for 1 hour
  13. temperatureunder reflux
  14. customthe solvent was removed under reduced pressure
  15. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-c00f77d27c59422d9ba5851087654ad3
Source dataset
uspto-grants-1976_06
Patent number
US03961062

Reaction notes

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