Triethylamine → HCID 10991490, compound

HRID 377536Notes

Reaction equation

HRID 377536 reaction equation
[CH3:1][CH:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)O[C:4](=[O:18])[CH2:3]1.C(N(CC)CC)C.[NH:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[NH2:27]>ClCCl>[CH2:31]([O:30][C:28]([NH:26][N:27]1[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:15])([F:16])[F:17])[CH:9]=2)=[CH:7][CH:2]([CH3:1])[CH2:3][C:4]1=[O:18])=[O:29])[CH3:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 11054254HCID 11054254, compound

Product 1

HCID 10991490HCID 10991490, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4 g (16 mmol) of 3,4-dihydro-4-methyl-6-(3'-trifluoromethylphenyl)-2-(1H)-pyrone in 100 ml dichloromethane is treated with 5.6 ml of triethylamine and 7.31 g (70 mmol) of ethyl hydrazinoformate, and the mixture is refluxed for 8 hours. After cooling, the reaction solution is washed alternately with distilled H2O, dilute HCl and distilled H2O, dried over Na2SO4 and concentrated on a rotary evaporator. The oil which remains is taken up in 150 ml of toluene, the solution is treated with a spatula-tip full of PTSA and the mixture is refluxed on a water separator until the reaction is complete. For working-up, the reaction solution is washed first with dilute K2CO3 solution and then with distilled H2O and subsequently dried over Na2SO4. The oil obtained after the solvent has been evaporated in vacuo is purified by column chromatography on silica gel (eluent: toluene:acetone=95:5).

Workup

  1. temperaturethe mixture is refluxed for 8 hours
  2. temperatureAfter cooling
  3. washthe reaction solution is washed alternately with distilled H2O, dilute HCl
  4. distillationdistilled H2O
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated on a rotary evaporator
  7. additionthe solution is treated with a spatula-tip full of PTSA
  8. temperaturethe mixture is refluxed on a water separator until the reaction
  9. washthe reaction solution is washed first with dilute K2CO3 solution
  10. dry with materialwith distilled H2O and subsequently dried over Na2SO4
  11. customThe oil obtained after the solvent
  12. customhas been evaporated in vacuo
  13. customis purified by column chromatography on silica gel (eluent: toluene:acetone=95:5)

Sources & evidence

ORD record
ord-bedbd77010e744fd96baa7c7fefe6cdc
Source dataset
uspto-grants-2000_02
Patent number
US06028033

Reaction notes

Loading…