Acetonitrile → 4-Fluoro-4'-(N-propyl-carbamyloxy)-alpha-ethyl-benzhydrol

HRID 1284930

Reaction equation

HRID 1284930 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([CH2:15][CH3:16])([OH:14])[C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH2:19]([N:22]=[C:23]=[O:24])[CH2:20][CH3:21].C(=O)([O-])[O-].[K+].[K+].C(#N)C>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([CH2:15][CH3:16])([OH:14])[C:7]2[CH:12]=[CH:11][C:10]([O:13][C:23](=[O:24])[NH:22][CH2:19][CH2:20][CH3:21])=[CH:9][CH:8]=2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 61033Propyl isocyanateHCID 147273204-Fluoro-4'-hydroxy-alpha-ethyl-benzhydrol

Product 1

HCID 147273274-Fluoro-4'-(N-propyl-carbamyloxy)-alpha-ethyl-benzhydrol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

12.3 g. of 4-fluoro-4'-hydroxy-α-ethyl-benzhydrol, 4.68 g. of n-propyl-isocyanate and 0.7 g. of anhydrous, powdered potassium carbonate in 61 ml. of acetonitrile containing 15 μlit. of a 50% aqueous ethanol solution are refluxed under stirring. When the reaction is complete, the reaction mixture is cooled to room temperature, potassium carbonate is filtered off and acetonitrile is distilled off under reduced pressure. The residue is dissolved in benzene, the benzene solution is shaken with a 5% aqueous sodium hydroxide solution and washed to neutral with water. The organic phase is dried over anhydrous magnesium sulfate, filtered, and benzene is distilled off under reduced pressure. Crystallization of the residue from a mixture of ethyl acetate and n-hexane yields 13.6 g. of the desired compound, melting at 107° to 108° C.

Workup

  1. filtrationpotassium carbonate is filtered off
  2. distillationacetonitrile is distilled off under reduced pressure
  3. dissolutionThe residue is dissolved in benzene
  4. stirringthe benzene solution is shaken with a 5% aqueous sodium hydroxide solution
  5. washwashed to neutral with water
  6. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. distillationbenzene is distilled off under reduced pressure
  9. customCrystallization of the residue
  10. additionfrom a mixture of ethyl acetate and n-hexane
  11. customyields 13.6 g

Sources & evidence

ORD record
ord-4d11fe74511e4c3eb171abfda8490584
Source dataset
uspto-grants-1986_01
Patent number
US04564630

Linked notes

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