Niclosamide → 4-Chloro-2-(2-chloro-4-nitrophenylcarbamoyl)phenyl benzoate

HRID 1509840

Reaktionsgleichung

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:21])=[C:6]([CH:20]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1[Cl:19])=[O:8].[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:22]([O:21][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:20][C:6]=1[C:7](=[O:8])[NH:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1[Cl:19])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

A suspension of 5-Chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide (1.27 g., 3.88 mmol) in pyridine (15 mL) was treated with 4-dimethylaminopyridine (30 mg) and benzoyl chloride (0.49 mL, 4.27 mmol) was introduced dropwise. The suspension was warmed to 50° C. for one hour then cooled to room temperature and stirred for 17 hours. The reaction mixture was partitioned between 1N aqueous HCl and ethyl acetate. The ethyl acetate phase was washed with water, then brine, dried over magnesium sulfate, and concentrated to an off-white solid. This was recrystallized from ethyl acetate/hexanes. 1HNMR (500 MHz, DMSO-d6): δ7.70 (M, 3H), 7.73 (m, 2H), 7.89 (m, 1H), 7.93 (M, 1H), 8.19 (m, 1H), 8.32 (m, 1H), 10.60 (s, 1H).

Aufarbeitung

additionwas introduced dropwise
temperaturethen cooled to room temperature
customThe reaction mixture was partitioned between 1N aqueous HCl and ethyl acetate
washThe ethyl acetate phase was washed with water
dry with materialbrine, dried over magnesium sulfate
concentrationconcentrated to an off-white solid
customThis was recrystallized from ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag: ord-c46173826d29412897e87d842c4660f2
Quelldatensatz: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08211882B2

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