Ethanol → HCID 178527892, compound

To a stirred solution of picolamide (1.50 g, 12.3 mmol) in N,N-dimethylformamide (20 mL) was added tert-butoxybis(dimethylamino)methane (5.2 mL, 25 mmol). The mixture was refluxed for 2.5 hours and then concentrated. The resulting viscous brown oil was taken up in a 0.5 M solution of sodium ethoxide in ethanol (50 mL, 25 mmol). Thiourea (0.72 g, 9.5 mmol) was added and the solution was refluxed for 2.5 hours. The reaction was concentrated and the residue partitioned between ethyl acetate and dilute aqueous sodium hydroxide solution. The aqueous layer was washed twice with ethyl acetate and neutralized with 1 N aqueous hydrochloric acid. The resulting precipitate was filtered off and rinsed with water. Vacuum oven dying afforded 0.72 g (40%) of crude product as a fine brown solid. This material was used without further purification in the next step.

1. temperatureThe mixture was refluxed for 2.5 hours
2. concentrationconcentrated
3. temperaturethe solution was refluxed for 2.5 hours
4. concentrationThe reaction was concentrated
5. customthe residue partitioned between ethyl acetate and dilute aqueous sodium hydroxide solution
6. washThe aqueous layer was washed twice with ethyl acetate and neutralized with 1 N aqueous hydrochloric acid
7. filtrationThe resulting precipitate was filtered off
8. washrinsed with water

ORD record

ord-affc88474bc94a0cbf22fbe6dd86aa5f

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07034031B2