Hydrochloric Acid → 3-(5-Cyano-pyridin-2-ylsulfanyl)-benzoic acid

HRID 2266994Notizen

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:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=1.Cl>CN(C)C=O>[C:18]([C:17]1[CH:20]=[CH: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])=[N:15][CH:16]=1)#[N:19]

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 6-chloro-nicotinonitrile (1.00 g, 7.22 mmol). Warm gradually to ambient temperature. After 18 hours, add 1N aqueous hydrochloric acid (200 mL). Filter resulting precipitate, washing with water and hexanes to yield the title compound as a tan solid (1.25 g, 68%): 1H NMR (DMSO-d6) δ 7.22 (d, 1H), 7.67 (t, 1H), 7.88 (dt, 1H), 8.07-8.12 (m, 3H), 8.82 (dd, 1H), 13.30 (bs, 1H).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-07b93c78d4494607a739c9ed84f4e433
Quelldatensatz: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07858646B2

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