Sodium Cyanide → HCID 67326339, compound

HRID 1397293Notes

Reaction equation

[C-:1]#[N:2].[Na+].Cl.[CH3:5][NH:6][CH3:7].[C:8]1([C:14]2[N:15]=[C:16]([CH:19]=O)[S:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O.CO>[CH3:5][N:6]([CH3:7])[CH:19]([C:16]1[S:17][CH:18]=[C:14]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:15]=1)[C:1]#[N:2]

Participants

Conditions

Temperature: -25 °C

Procedure

Sodium cyanide (124 mg, 2.53 mmol) was added to a solution of dimethylamine hydrochloride (280 mg, 3.43 mmol) in water (10 mL), followed by the addition of a solution of 4-phenylthiazole-2-carbaldehyde (400 mg, 2.11 mmol) in methanol (20 mL) while maintaining the temperature at −25° C. The reaction mixture was further stirred for 4 h at same temperature, then it was diluted with water and the organic product was extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to get the crude product, which was purified by column chromatography (silica 60-120 mesh, eluant 15% EtOAc in petroleum ether), to yield 2-(dimethylamino)-2-(4-phenylthiazol-2-yl)acetonitrile (160 mg, yield 31%). 1H NMR (400 MHz, CDCl3) δ 7.97-7.94 (m, 2H), 7.57 (s, 1H), 7.46-7.42 (m, 2H), 7.38-7.33 (m, 1H), 5.12 (s, 1H), 2.50 (s, 6H). MS (ESI) m/z: Calculated for C13H13N3S: 243.08. found: 244.2 (M+H)+.

Workup

extractionthe organic product was extracted with EtOAc
washThe organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customto get the crude product, which
customwas purified by column chromatography (silica 60-120 mesh, eluant 15% EtOAc in petroleum ether)

Sources & evidence

ORD record: ord-838b29350e474646a9d96620cde0452e
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901156B2

Reaction notes

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