Hydrochloric Acid → 3-[(4-Cyanopyridin-2-YL)sulfanyl]benzoic acid

HRID 2266993

Reaktionsgleichung

[H-].[Na+].[SH:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8].Cl[C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][N:21]=1)[C:17]#[N:18].Cl>CN(C)C=O>[C:17]([C:16]1[CH:19]=[CH:20][N:21]=[C:14]([S:3][C:4]2[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=2)[C:7]([OH:9])=[O:8])[CH:15]=1)#[N:18]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Add sodium hydride (60% dispersion in mineral oil, 635 mg, 15.88 mmol) to a solution of 3-mercapto-benzoic acid (1.11 g, 7.22 mmol) in dimethylformamide (50 mL) chilled to 0° C. and stir. After 10 minutes add 2-chloro-isonicotinonitrile (1.00 g, 7.22 mmol). Warm gradually to ambient temperature. After 18 hours, add 1N aqueous hydrochloric acid (200 mL). Filter the resulting precipitate, washing with water and hexanes to yield the title compound as a tan solid (920 mg, 50%): 1H NMR (DMSO-d6) δ 7.62-7.66 (m, 3H), 7.84 (d, 1H), 8.03-8.08 (m, 2H), 8.62 (d, 1H), 13.26 (bs, 1H).

Aufarbeitung

temperatureWarm gradually to ambient temperature
filtrationFilter the resulting precipitate
washwashing with water and hexanes

Quellen und Nachweise

ORD-Eintrag: ord-5da088957feb4c6f9393d2d79fae43c3
Quelldatensatz: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07858646B2

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