1-Bromopropane → HCID 23659148, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1,3,4-thiadiazole-2,5-dithiol (601 mg, 4.00 mmol) in DMF and benzene (6 ml, 1/1) was added NaH (60% dispersion in mineral oil, 176 mg, 4.40 mmol) slowly at 0° C. under nitrogen atmosphere. The resulting suspension was stirred at 0° C. for 15 minutes and then to the mixture was added bromopropane (492 mg, 2.00 mmol). The reaction was stirred at rt for 1 hr. To the reaction was added NaH (60% dispersion in mineral oil, 176 mg, 4.40 mmol) slowly at 0° C. and stirred for 15 minutes after addition. Then, 3-chloropyrazine-2-carbonitrile (557 mg, 4.00 mmol) was added to the mixture and the reaction was stirred at 50° C. under N2 overnight. The reaction was then cooled to room temperature and quenched with saturated NH4Cl solution and extracted with EtOAc. The combined organic layers were washed with water, brine and dried over MgSO4. Removal of solvent gave the crude product which was purified by chromatography to give the title compound as an off-white solid.

Provenance & Evidence