Octanoyl chloride → HCID 20271342, Verbindung

HRID 485068Notizen

Reaktionsgleichung

[C:1](Cl)(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[NH:23][N:22]=[C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=2)[N:20]=1.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>O1CCOCC1.O>[CH3:31][O:30][C:26]1[CH:25]=[C:24]([C:21]2[N:20]=[C:19]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][O:11][C:1](=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[NH:23][N:22]=2)[CH:29]=[CH:28][CH:27]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

A solution of octanoyl chloride (4.25 ml, 25 mmole) in dioxane (10 ml) is added dropwise during ten minutes into a stirred suspension of 5-(2-hydroxymethylphenyl)-3-(3-methoxyphenyl)-1H-1,2,4-triazole (2.81 g, 10 mmole) and triethylamine (4.2 ml, 30 mmole) in dioxane (50 ml). After 1 hour, 8% NaHCO3 (50 ml) is added and the reaction mixture is heated to 50° C. for two hours, cooled to room temperature, diluted with water (60 ml) and extracted with methylene chloride. The organic extracts are washed with water, dried over Na2SO4 and concentrated to dryness yielding a raw residue which is purified by silica-gel column chromatography eluting with a mixture 0% to 10% ethyl acetate in toluene and crystallized from isopropyl ether/petroleum ether. Yield: 56.5%. M.p. 61° C. and 87° C. (as a mixture of crystal forms).

Aufarbeitung

temperaturecooled to room temperature
extractionextracted with methylene chloride
washThe organic extracts are washed with water
dry with materialdried over Na2SO4
concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag: ord-30b3b02c81214f118962a9611e4cda54
Quelldatensatz: uspto-grants-1985_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04535090

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