Methanol → Bosentan

HRID 1020776

Reaktionsgleichung

Reaktionsgleichung von HRID 1020776
CO.[CH3:3][C:4]([C:7]1[CH:8]=[CH:9][C:10]([S:13]([NH:16][C:17]2[C:18]([O:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:39]=3[O:40][CH3:41])=[C:19]([O:29][CH2:30][CH2:31][OH:32])[N:20]=[C:21]([C:23]3[N:24]=[CH:25][CH:26]=[CH:27][N:28]=3)[N:22]=2)(=[O:15])=[O:14])=[CH:11][CH:12]=1)([CH3:6])[CH3:5].[K]>ClCCl>[CH3:6][C:4]([C:7]1[CH:12]=[CH:11][C:10]([S:13]([NH:16][C:17]2[C:18]([O:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:39]=3[O:40][CH3:41])=[C:19]([O:29][CH2:30][CH2:31][OH:32])[N:20]=[C:21]([C:23]3[N:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[N:22]=2)(=[O:14])=[O:15])=[CH:9][CH:8]=1)([CH3:3])[CH3:5]

Komponenten

4

Edukt 2

HCID 887MethanolHCID 66744754Bosentan potassium

Produkt 1

HCID 104865Bosentan

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Methanol (200 mL) and dichloromethane (200 ml) were added to the bosentan potassium as obtained in Step 2. The mixture was heated to 50° C. to 55° C. The mixture was stirred for 20 minutes at the same temperature and dichloromethane (˜150 mL) was recovered at atmospheric pressure at 40° C. to 55° C. Ethyl acetate (800 mL) was added to the residue at 50° C. to 55° C. The reaction mixture was cooled to 20° C. to 25° C., stirred for 3 hours, filtered and washed with a mixture of methanol (20 mL) and ethyl acetate (80 mL). The solid obtained was dried under vacuum at 55° C. to 60° C. until the loss on drying was not more than 2.0% w/w to obtain the title compound.

Aufarbeitung

  1. customas obtained in Step 2
  2. temperatureThe mixture was heated to 50° C. to 55° C
  3. customwas recovered at atmospheric pressure at 40° C. to 55° C
  4. additionEthyl acetate (800 mL) was added to the residue at 50° C. to 55° C
  5. temperatureThe reaction mixture was cooled to 20° C. to 25° C.
  6. filtrationfiltered
  7. washwashed with a mixture of methanol (20 mL) and ethyl acetate (80 mL)
  8. customThe solid obtained
  9. customwas dried under vacuum at 55° C. to 60° C. until the loss
  10. customon drying

Quellen und Nachweise

ORD-Eintrag
ord-239fd76c7f73405cba59a57c90685156
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716477B2

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