Trifluoroacetic acid → HCID 19897014, compound

HRID 1196975Notes

Reaction equation

HRID 1196975 reaction equation
Cl.[NH2:2][CH:3]([CH3:16])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][CH3:15])=[CH:8][CH:7]=1)=O.[CH3:17][N:18]=[C:19]=[O:20].C(N(CC)CC)C.FC(F)(F)C(O)=O>CC(C)=O>[CH2:12]([C:9]1[CH:10]=[CH:11][C:6]([C:4]2[N:18]([CH3:17])[C:19](=[O:20])[NH:2][C:3]=2[CH3:16])=[CH:7][CH:8]=1)[CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 19896993HCID 19896993, compound

Product 1

HCID 19897014HCID 19897014, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Amino-4'-n-butylpropiophenone hydrochloride (5.36 g, 22.2 mmol) was suspended in acetone (180 ml) under ice-cooling, and methyl isocyanate (1.61 g, 28.2 mmol) was added thereto. After addition of triethylamine (4.49 g, 44.5 mmol), the mixture was stirred for 40 minutes under ice-cooling. Trifluoroacetic acid (16 ml) was added thereto, and the mixture was stirred for 5 hours at room temperature. The solvent was removed by evaporation under vacuum, and the residue was taken in dichloromethane. The organic mixture was washed successively with water and saturated aqueous sodium chloride, and dried over magnesium sulfate. Evaporation of the solvent provided a crude product, which was purified by column chromatography (chloroform/ ethanol=50/1 (v/v)) and recrystalization (hexane-ethyl acetate) to give the title compound. Yield: 3.85 g (71%), m.p. 180°-180.5° C.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred for 5 hours at room temperature
  4. customThe solvent was removed by evaporation under vacuum
  5. washThe organic mixture was washed successively with water and saturated aqueous sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. customEvaporation of the solvent
  8. customprovided a crude product, which
  9. customwas purified by column chromatography (chloroform/ ethanol=50/1 (v/v)) and recrystalization (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-72780fe6238e4000a59fd18fdd4632f3
Source dataset
uspto-grants-1992_05
Patent number
US05116858

Reaction notes

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