1,2-Dibromoethane → 1-(4-Phenylthiazol-2-yl)cyclopropanecarbonitrile

HRID 1397297Notes

Reaction equation

[OH-].[Na+].[C:3]1([C:9]2[N:10]=[C:11]([CH2:14][C:15]#[N:16])[S:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:18][CH2:19]Br>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl>[C:3]1([C:9]2[N:10]=[C:11]([C:14]3([C:15]#[N:16])[CH2:19][CH2:18]3)[S:12][CH:13]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Benzyltriethyl ammonium chloride (34 mg, 0.15 mmol) and 50% aqueous NaOH solution (0.59 g dissolved in 1 mL of water) were added to a solution of 2-(4-phenylthiazol-2-yl)acetonitrile (0.3 g, 1.5 mmol) in CH2Cl2 (10 mL). The reaction mixture was cooled at 0° C. and 1,2-dibromoethane (0.15 mL, 1.79 mmol) was added dropwise. The reaction mixture was allowed to warm up to room temperature and stirred for 10 h. The reaction mixture was diluted with CH2Cl2 and the organic layer was washed with H2O and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel 60-120 mesh, eluent 5% EtOAc in petroleum ether) to afford 1-(4-phenylthiazol-2-yl)cyclopropanecarbonitrile (0.14 g, yield 41%) as an off-white solid. 1H NMR (300 MHz, CDCl3) δ 7.86-7.83 (m, 2H), 7.45-7.34 (m, 4H), 2.02-1.95 (m, 2H), 1.93-1.86 (m, 2H). MS (ESI) m/z: Calculated for C13H10N2S: 226.06. found: 227.2 (M+H)+.

Workup

temperatureto warm up to room temperature
washthe organic layer was washed with H2O and brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography (silica gel 60-120 mesh, eluent 5% EtOAc in petroleum ether)

Sources & evidence

ORD record: ord-dbb2b232637b4d778047fb5b0f976f8e
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901156B2

Reaction notes

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