Water → Bicalutamide

HRID 1269473Notes

Reaction equation

HRID 1269473 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:23])[C:11]([OH:22])([CH3:21])[CH2:12][S:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[CH:5][C:4]=1[C:24]([F:27])([F:26])[F:25])#[N:2].[OH2:28].[OH:29]OS([O-])=O.[K+]>CO>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:23])[C:11]([OH:22])([CH3:21])[CH2:12][S:13]([C:14]2[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=2)(=[O:29])=[O:28])=[CH:5][C:4]=1[C:24]([F:27])([F:26])[F:25])#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 9800987Bicalutamide sulfideHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 2375Bicalutamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 40 g (0.1 mol) of N-[4-cyano-3-trifluoromethyl-phenyl]-3-[4-fluorophenyl-thio]-2-hydroxy-2-methyl-propionamide in 600 ml of methanol and 400 ml of water 100 g (0.16 mol) of Oxone® oxidizing agent [2KHSO5KHSO4K2SO4 salt] was added. The reaction mixture was stirred at 25° C. for 6 h, then the methanol was distilled off under diminished pressure and the residue was extracted twice with 500 ml of dichloromethane. The organic layer was washed twice with 400 ml of 10% aqueous sodium thiosulfate solution, then with brine, dried over sodium sulfate and concentrated under diminished pressure. The residue was recrystallized from a 1:4 mixture of ethyl acetate/petroleum ether, which has a boiling range of 40–70° C.

Workup

  1. additionwas added
  2. distillationthe methanol was distilled off under diminished pressure
  3. extractionthe residue was extracted twice with 500 ml of dichloromethane
  4. washThe organic layer was washed twice with 400 ml of 10% aqueous sodium thiosulfate solution
  5. dry with materialwith brine, dried over sodium sulfate
  6. concentrationconcentrated under diminished pressure
  7. customThe residue was recrystallized from a 1:4 mixture of ethyl acetate/petroleum ether, which

Sources & evidence

ORD record
ord-fb8594b35111463695d5b9ec3615ff96
Source dataset
uspto-grants-2007_04
Patent number
US07199257B1

Reaction notes

Loading…