Hydrochloric Acid → HCID 20238646, compound

HRID 364962Notes

Reaction equation

HRID 364962 reaction equation
[N:1]1[O:5][N:4]=[C:3]2[C:6]([CH:10]3[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:14]([C:21]([F:24])([F:23])[F:22])[NH:13][C:12]([CH:25](OCC)[O:26]CC)=[C:11]3[C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:7][CH:8]=[CH:9][C:2]=12.Cl.C(OCC)(=O)C.CC(O)C>O1CCCC1>[N:1]1[O:5][N:4]=[C:3]2[C:6]([CH:10]3[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:14]([C:21]([F:24])([F:23])[F:22])[NH:13][C:12]([CH:25]=[O:26])=[C:11]3[C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:7][CH:8]=[CH:9][C:2]=12

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 8857Ethyl AcetateHCID 20238652HCID 20238652, compound

Product 1

HCID 20238646HCID 20238646, compoundYield 7.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of diethyl 4-(4-benzofurazanyl)-2-(diethoxymethyl)-1,4-dihydro-6-(trifluoromethyl)-3,5-pyridinedicarboxylate (7.6 g, 14.5 mmoles) in tetrahydrofuran (100 ml) was added 25% aqueous hydrochloric acid solution (100 ml) and the resulting solution heated at reflux. After 1.5 hours the cooled solution was poured into ethyl acetate (200 ml). The organic phase was separated and washed with water, saturated aqueous sodium bicarbonate solution, brine and dried (MgSO4). Evaporation of the solvent left an oil (7.5 g) which was purified by chromatography on silica (300 g) using ether-petroleum ether (60°-80°) as eluent. The major component was obtained as an oil which gave a solid on trituration with 2-propanol. Recrystallisation from 2-propanol gave the title compound (0.45 g) as yellow crystals mp 94°-5°.

Workup

  1. temperaturethe resulting solution heated
  2. temperatureat reflux
  3. customThe organic phase was separated
  4. washwashed with water, saturated aqueous sodium bicarbonate solution, brine
  5. dry with materialdried (MgSO4)
  6. customEvaporation of the solvent
  7. waitleft an oil (7.5 g) which
  8. customwas purified by chromatography on silica (300 g)
  9. customether-petroleum ether (60°-80°)
  10. customThe major component was obtained as an oil which
  11. customRecrystallisation from 2-propanol

Sources & evidence

ORD record
ord-50dfeef0d9c44883a40474af5d8f2e9b
Source dataset
uspto-grants-1986_08
Patent number
US04607041

Reaction notes

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