Trifluoroacetic acid → HCID 19897021, compound

HRID 1196978Notes

Reaction equation

HRID 1196978 reaction equation
Cl.[NH2:2][CH:3]([CH3:20])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][CH:7]=1)=O.[CH:21]1([N:27]=[C:28]=[O:29])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.C(N(CC)CC)C.FC(F)(F)C(O)=O>CC(C)=O>[CH2:13]([O:12][C:9]1[CH:10]=[CH:11][C:6]([C:4]2[N:27]([CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[C:28](=[O:29])[NH:2][C:3]=2[CH3:20])=[CH:7][CH:8]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 18502Cyclohexyl isocyanateHCID 19897004HCID 19897004, compound

Product 1

HCID 19897021HCID 19897021, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Amino-4'-benzyloxypropiophenone hydrochloride (349 mg, 1.20 mmol) was suspended in acetone (30 ml) under ice-cooling, and cyclohexyl isocyanate (204 mg, 1.62 mmol) was added thereto. Triethylamine (377 mg, 3.73 mmol) was then added, and the mixture was stirred for one hour under ice-cooling. After addition of trifluoroacetic acid (2 ml), the mixture was stirred for 6 days at room temperature. The solvent was removed by evaporation in vacuo, and the residue was extracted with dichloromethane. The extract was washed successively with water and saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. Evaporation of the solvent provided a crude product, which was purified by column chromatography (chloroform/ ethanol=50/1 (v/v)) and recrystalization (ethanol-chloroform) to give the title compound. Yield: 240 mg (55%), m.p. 262° C.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred for 6 days at room temperature
  4. customThe solvent was removed by evaporation in vacuo
  5. extractionthe residue was extracted with dichloromethane
  6. washThe extract was washed successively with water and saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customEvaporation of the solvent
  9. customprovided a crude product, which
  10. customwas purified by column chromatography (chloroform/ ethanol=50/1 (v/v)) and recrystalization (ethanol-chloroform)

Sources & evidence

ORD record
ord-8d31af39086b4792ba8b0fb8ccc3eb7c
Source dataset
uspto-grants-1992_05
Patent number
US05116858

Reaction notes

Loading…