Ammonia → (4-Phenyl-1,3-thiazol-2-yl)acetonitrile

HRID 1397203Notes

Reaction equation

Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[C:11]([CH2:13][C:14]([NH2:16])=[S:15])#[N:12].N>CCO>[C:5]1([C:3]2[N:16]=[C:14]([CH2:13][C:11]#[N:12])[S:15][CH:2]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-bromoacetophenone (2 g, 10 mmol) and 2-cyanothioacetamide (1 g, 10 mmol) in EtOH (25 mL) was heated to 80° C. for 4 h. The reaction mixture was cooled to room temperature and poured into an aqueous ammonia solution (final pH was >7). The mixture was then extracted with EtOAc and the organic layer was washed with H2O and brine. Solvent was removed under reduced pressure and the crude product was purified by flash column chromatography (silica gel 230-400 mesh, eluent 8% EtOAc in petroleum ether) to afford 2-(4-phenylthiazol-2-yl)acetonitrile (1.5 g, yield 75%) as a yellow solid: 1H NMR (300 MHz, CDCl3) δ 7.88-7.91 (m, 2H), 7.49 (s, 1H), 7.27-7.48 (m, 3H), 4.19 (s, 2H). MS (ESI) m/z: Calculated for C11H8N2S: 200.04. found: 201.2 (M+H)+.

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionThe mixture was then extracted with EtOAc
washthe organic layer was washed with H2O and brine
customSolvent was removed under reduced pressure
customthe crude product was purified by flash column chromatography (silica gel 230-400 mesh, eluent 8% EtOAc in petroleum ether)

Sources & evidence

ORD record: ord-bb3554c3daec4f28851519ffa4048c08
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901156B2

Reaction notes

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