Benzoyl isothiocyanate → 1-Benzoyl-3-[2-methoxy-5-(tetrahydropyran-4-yl)-phenyl]-thiourea

HRID 1582104Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1582104
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:5][C:4]=1[NH2:15].[C:16]([N:24]=[C:25]=[S:26])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC(C)=O>[C:16]([NH:24][C:25]([NH:15][C:4]1[CH:5]=[C:6]([CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])=[S:26])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

4

Edukt 2

HCID 68284Benzoyl isothiocyanateHCID 219192622-Methoxy-5-(tetrahydropyran-4-yl)-phenylamine

Produkt 1

HCID 227195711-Benzoyl-3-[2-methoxy-5-(tetrahydropyran-4-yl)-phenyl]-thioureaAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 2.75 g (13.3 mmol) 2-methoxy-5-(tetrahydro-pyran-4-yl)-phenylamine in 60 ml acetone was added dropwise a solution of 2.04 ml (15.2 mmol) benzoyl isothiocyanate in 30 ml acetone and stirring continued for 30 minutes at room temperature. The mixture was then concentrated in vacuo. Flash chromatography (1/1 ethyl acetate/hexane) followed by trituration in ether afforded 3.25 g (66%) 1-benzoyl-3-[2-methoxy-5-(tetrahydro-pyran-4-yl)-phenyl]-thiourea as a white solid. ES-MS m/e (%): 371 (M+H+, 100).

Aufarbeitung

  1. concentrationThe mixture was then concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ebd486e6304f4d9186581c963c6d0546
Quelldatensatz
uspto-grants-2004_05
Patentnummer
US06734179B2

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