Methane → Bicalutamide sulfide

HRID 1269471

Reaktionsgleichung

Reaktionsgleichung von HRID 1269471
[F:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[OH-].[Na+].[C:11]([C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:30])[C:21]([OH:29])([CH3:28])[CH2:22]OS(C)(=O)=O)=[CH:15][C:14]=1[C:31]([F:34])([F:33])[F:32])#[N:12].Cl.C>O.C(O)(C)C>[C:11]([C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:30])[C:21]([OH:29])([CH3:28])[CH2:22][S:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:15][C:14]=1[C:31]([F:32])([F:34])[F:33])#[N:12]

Komponenten

8

Edukt 5

HCID 297MethaneHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 677894-FluorothiophenolHCID 12148451N-[4-cyano-3-trifluoromethyl-phenyl]-2-hydroxy-3-methanesulfonyloxy-2-methyl-propionamide

Produkt 1

HCID 9800987Bicalutamide sulfide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

Under nitrogen, to a solution of 25.6 g (0.20 mol) of 4-fluorthiophenol in 500 ml of isopropanol 8.4 g (0.20 mol) of sodium hydroxide in 400 ml of water was added. The mixture was stirred at 25° C. for 2 h, then 58.6 g (16 mmol) of N-[4-cyano-3-trifluoromethyl-phenyl]-2-hydroxy-3-(methanesulfonyloxy)-2-methyl-propionamide in 500 ml of isopropanol was added. Then the mixture was stirred at 25° C. for 5 h, then the pH was adjusted to neutral with concentrated hydrochloric acid and treated with charcoal at reflux temperature. Most of the isopropanol was evaporated in vacuum and 250 ml of 2% aqueous sodium hydroxide solution was added to the residue under vigorous stirring, then the crystalline mixture was left for 1 h, then filtered and washed with water. The dried crystals were recrystallized from a 1:4 mixture of ethyl acetate/petroleum ether, which has a boiling range of 40–70° C.

Aufarbeitung

  1. stirringThen the mixture was stirred at 25° C. for 5 h
  2. temperatureat reflux temperature
  3. customMost of the isopropanol was evaporated in vacuum and 250 ml of 2% aqueous sodium hydroxide solution
  4. additionwas added to the residue under vigorous stirring
  5. waitthe crystalline mixture was left for 1 h
  6. filtrationfiltered
  7. washwashed with water
  8. customThe dried crystals were recrystallized from a 1:4 mixture of ethyl acetate/petroleum ether, which

Quellen und Nachweise

ORD-Eintrag
ord-c36812cca5604aec8889a57aaec81e82
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199257B1

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