Methanol → HCID 59823517, Verbindung

HRID 1426865Notizen

Reaktionsgleichung

[H-].[Na+].[NH2:3][C:4]1[C:9]([CH3:10])=[CH:8][C:7]([OH:11])=[C:6]([CH3:12])[CH:5]=1.Cl[C:14]1[S:15][C:16]([Cl:20])=[C:17]([Cl:19])[N:18]=1.CO>CN(C)C=O.C(OCC)(=O)C.O>[Cl:19][C:17]1[N:18]=[C:14]([O:11][C:7]2[C:6]([CH3:12])=[CH:5][C:4]([NH2:3])=[C:9]([CH3:10])[CH:8]=2)[S:15][C:16]=1[Cl:20]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

1.3 g (33 mmol) sodium hydride (60% in oil) were added portionwise to a solution of 4.1 g (30.0 mmol) of 4-amino-2,5-dimethylphenol in 30 ml of dimethylformamide. After the gas evolution has stopped, 5.6 g (30 mmol) of 2,4,5-trichloro-1,3-thiazole were added and the reaction mixture was stirred for 1 h at 100° C. At ambient temperature 0.5 ml methanol, 10 ml of water and 100 ml of ethyl acetate were added successively. The organic layer was separated, the watery layer extracted with ethyl acetate and the combined organic layers were dried over magnesium sulfate. Concentration in vacuo and column chromatographie (petroleum ether/acetone 4/1) yielded 4.8 g (16.6 mmol, 55%) of 4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylaniline log P (pH=2.3)=3.4

Aufarbeitung

customThe organic layer was separated
extractionthe watery layer extracted with ethyl acetate
dry with materialthe combined organic layers were dried over magnesium sulfate
concentrationConcentration in vacuo and column chromatographie (petroleum ether/acetone 4/1)

Quellen und Nachweise

ORD-Eintrag: ord-cc9423bda7674ec0b551325e47a5ddde
Quelldatensatz: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08933107B2

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