Hexane → 1-Benzoyl-3-(5-methoxy-2-morpholin-4-yl-pyridin-4-yl)-thiourea

HRID 917408Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 917408
[CH3:1][O:2][C:3]1[C:4]([NH2:15])=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[N:7][CH:8]=1.[C:16]([N:24]=[C:25]=[S:26])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCCCCC>CC(C)=O>[C:16]([NH:24][C:25]([NH:15][C:4]1[C:3]([O:2][CH3:1])=[CH:8][N:7]=[C:6]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:5]=1)=[S:26])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 8058HexaneHCID 68284Benzoyl isothiocyanateHCID 589627015-Methoxy-2-morpholin-4-yl-pyridin-4-ylamine

Produkt 1

HCID 589626971-Benzoyl-3-(5-methoxy-2-morpholin-4-yl-pyridin-4-yl)-thioureaAusbeute 66,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a stirred solution of 27.5 g (132 mmol) 5-methoxy-2-morpholin-4-yl-pyridin-4-ylamine in 400 ml acetone was added dropwise 19.5 ml (145 mmol) benzoyl isothiocyanate at room temperature. The reaction mixture then heated at reflux for 90 min before being cooled to room temperature and poured onto 400 ml hexane and stirred for 5 min. The resulting crystals were collected by filtration, washed with hexane and dried to afford 32.5 g (66%) 1-benzoyl-3-(5-methoxy-2-morpholin-4-yl-pyridin-4-yl)-thiourea as a brown crystalline solid. ES-MS m/e (%): 373 (M+H+, 100).

Aufarbeitung

  1. temperatureThe reaction mixture then heated
  2. temperatureat reflux for 90 min
  3. filtrationThe resulting crystals were collected by filtration
  4. washwashed with hexane
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-016163aaed7b4acf890e68d293f20667
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07273865B2

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