Water → Bicalutamide

HRID 1269473

반응식

HRID 1269473 반응식
[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]

참가 물질

5

반응물 3

HCID 962WaterHCID 9800987Bicalutamide sulfideHCID 23707502Potassium hydroxy sulfite

생성물 1

HCID 2375Bicalutamide

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
25 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fb8594b35111463695d5b9ec3615ff96
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199257B1

연결된 노트

불러오는 중…