Triethylamine → HCID 54606663, compound

N-Hydroxyphthalimide (15.2 g) was dissolved in DMF (120 ml) and 4-chloromethyl-2-methyl-thiazole (18.4 g) was added. The mixture was cooled in an ice bath and a solution of triethylamine (28.6 ml) in DMF (30 ml) was added drop-wise. The cooling bath was removed and the reaction mixture was stirred at room temperature for 3 days. The mixture was poured into water (600 ml) and the precipitated material was isolated by filtration washed with water and dried in vacuo. This phthalimide intermediate (21.4 g) was refluxed in ethanol (150 ml) containing n-butylamine (7.7 ml) for 2.5 hours. The mixture was cooled to room temperature and 4M hydrochloric acid in diethyl ether (25 ml) was added. The mixture was placed at 0-5° C. over night at the resulting precipitated material was isolated by filtration and washed with cold ethanol and diethyl ether, affording the title compound (11.2 g) as a white crystalline material. 13C-NMR (DMSO-d6) δ 166.85, 147.15, 121.35, 70.03, 18.37.

1. temperatureThe mixture was cooled in an ice bath
2. customThe cooling bath was removed
3. additionThe mixture was poured into water (600 ml)
4. customthe precipitated material was isolated by filtration
5. washwashed with water
6. customdried in vacuo
7. temperatureThis phthalimide intermediate (21.4 g) was refluxed in ethanol (150 ml)
8. additioncontaining n-butylamine (7.7 ml) for 2.5 hours
9. temperatureThe mixture was cooled to room temperature
10. addition4M hydrochloric acid in diethyl ether (25 ml) was added
11. waitThe mixture was placed at 0-5° C. over night at the resulting
12. customprecipitated material
13. customwas isolated by filtration
14. washwashed with cold ethanol and diethyl ether

ORD record

ord-03c38a2025d449be8ae03836582dd9db

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08034811B2