Water → HCID 17992063, compound

Temperature

100 °C

Butyl lithium (2.4 M, 50 ml) in hexane was added to a solution of 2-chlorothiazole (12.43 g, 0.104 mol) in tetrahydrofuran (400 ml) at -78° C. under at atmosphere of nitrogen. The resultant solution was stirred for 5 minutes before propyl isocyanate (11.25 ml, 0.12 mol) was added and the reaction mixture was then stirred for a further 10 minutes before being hydrolysed with water (100 ml). The solvent was removed under reduced pressure and the residue extracted with ethyl acetate (2×400 ml). The combined organic extract was then washed with saturated sodium chloride solution, dried over magnesium sulphate and the solvent evaporated. Acetic acid (110 ml) was added to the residue and the solution warmed to about 100° C. whereupon zinc dust (11.8 g) was added and the mixture was refluxed for 1 hour. On cooling, the reaction mixture was made basic with ammonium hydroxide and then extracted into ethyl acetate (4×250 ml). The combined organic extract was washed with saturated sodium chloride solution, dried (MgSO4) and then concentrated. Flash chromatography of the residue on a silica gel column using ethyl acetate as eluant gave N-propylthiazole-5-carboxamide (12.2 g) as a pale yellow solid, m.pt. 86° C.

1. additionwas added
2. customThe solvent was removed under reduced pressure
3. extractionthe residue extracted with ethyl acetate (2×400 ml)
4. extractionThe combined organic extract
5. washwas then washed with saturated sodium chloride solution
6. dry with materialdried over magnesium sulphate
7. customthe solvent evaporated
8. additionAcetic acid (110 ml) was added to the residue
9. additionwas added
10. temperaturethe mixture was refluxed for 1 hour
11. temperatureOn cooling
12. extractionextracted into ethyl acetate (4×250 ml)
13. extractionThe combined organic extract
14. washwas washed with saturated sodium chloride solution
15. dry with materialdried (MgSO4)
16. concentrationconcentrated

ORD record

ord-e2c62a1570e24364bdf40ef64151b487

Source dataset

uspto-grants-1989_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04877802