Triethylamine → HCID 647033, compound

Temperature

5 °C

Under a nitrogen atmosphere, a stirred suspension of 2-(4-fluorophenyl)-2-(4-methylphenylsulfonyloxy)iminoacetonitrile (64.0 g, 0.2 mole) and triethylamine (61.8 g, 0.61 mole) in 1 l of absolute ethanol was cooled to 5° C. Ethyl 2-mercaptoacetate (26.8 g, 0.22 mole) was added dropwise over a four hour period. The reaction mixture was then stirred for 16 hours and warmed to room temperature. The reaction mixture was concentrated and poured into 2 l of ice water. The resultant precipitate was collected by filtration. The solid filter cake was washed with water and dried. The solid was dissolved in 1.5 l of boiling heptane, and the solution was slurried with silica gel. The hot mixture was filtered; on cooling the filtrate, the solid recrystallized and was collected by filtration, washed with heptane, and dried to give ethyl 3-(4-fluorophenyl)-4-amino-5-isothiazolecarboxylate (22.0 g, mp 137°-139° C.).

1. temperaturewarmed to room temperature
2. concentrationThe reaction mixture was concentrated
3. additionpoured into 2 l of ice water
4. filtrationThe resultant precipitate was collected by filtration
5. filtrationThe solid filter cake
6. washwas washed with water
7. customdried
8. dissolutionThe solid was dissolved in 1.5 l of boiling heptane
9. filtrationThe hot mixture was filtered
10. temperatureon cooling the filtrate
11. customthe solid recrystallized
12. filtrationwas collected by filtration
13. washwashed with heptane
14. customdried

ORD record

ord-890f4cb688164871bd3e176b443b7112

Source dataset

uspto-grants-1985_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04539328