Trifluoroacetic acid → HCID 19896995, compound

HRID 1196977Notes

Reaction equation

HRID 1196977 reaction equation
Cl.[NH2:2][CH:3]([CH3:19])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:8][CH:7]=1)=O.[CH:20]1([N:26]=[C:27]=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C(N(CC)CC)C.FC(F)(F)C(O)=O>CC(C)=O>[CH:20]1([N:26]2[C:4]([C:6]3[CH:11]=[CH:10][C:9]([O:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)=[CH:8][CH:7]=3)=[C:3]([CH3:19])[NH:2][C:27]2=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 18502Cyclohexyl isocyanateHCID 19896996HCID 19896996, compound

Product 1

HCID 19896995HCID 19896995, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Amino-4'-phenoxypropiophenone hydrochloride (459 mg, 1.65 mmol) was suspended in acetone (30 ml) under ice-cooling, and cyclohexyl isocyanate (278 mg, 2.22 mmol) was added thereto. Triethylamine (476 mg, 4.71 mmol) was added, and the mixture was stirred for 50 minutes under ice-cooling. After addition of trifluoroacetic acid (1.5 ml), the mixture was stirred for 3 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 (ethyl acetate) to give the title compound. Yield: 520 mg (90%), m.p. 198° C.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred for 3 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 (ethyl acetate)

Sources & evidence

ORD record
ord-d2654fe8b4b340c794084c6f1194092b
Source dataset
uspto-grants-1992_05
Patent number
US05116858

Reaction notes

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