Thiocyanatoacetic acid ethyl ester → 2-(cyclopropylmethylamino)-1,3-thiazol-4-one

Temperature

90 °C

A mixture of cyclopropylmethylammonium acetate (0.45 g, 3.44 mmol) and thiocyanato-acetic acid ethyl ester (0.5 g, 3.44 mmol) was heated to 90° C. for 2 h. The reaction mixture was partitioned between 6N HCl and dichloromethane. The layers were separated. The aqueous layer was made basic by the addition of 6N ammonium hydroxide, and then extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The aqueous layer was also concentrated to dryness and the residue was triturated with DMF. The DMF solution was filtered and concentrated to dryness. The residues were combined and purified on a silica gel column with 100% ethyl acetate to afford 2-cyclopropylmethylamino-thiazol-4-one (275 mg, 47%).

1. customThe reaction mixture was partitioned between 6N HCl and dichloromethane
2. customThe layers were separated
3. additionThe aqueous layer was made basic by the addition of 6N ammonium hydroxide
4. extractionextracted with dichloromethane
5. dry with materialThe organic layer was dried over sodium sulfate
6. concentrationconcentrated under reduced pressure
7. concentrationThe aqueous layer was also concentrated to dryness
8. customthe residue was triturated with DMF
9. filtrationThe DMF solution was filtered
10. concentrationconcentrated to dryness
11. custompurified on a silica gel column with 100% ethyl acetate

ORD record

ord-62547e3d71a24edbafbf1c59cca1ba08

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07241893B2