Chlorosuccinimide → HCID 15729141, compound

Temperature

40 °C

A mixture of 2-acetylamino-4-hydroxymethylthiazole (7.0 g) and N-chlorosuccinimide (6.5 g) in acetic acid (70 ml) was heated at 40° C. for 3.5 hours with stirring. The reaction mixture was concentrated under reduced pressure and the residue was added the aqueous sodium bicarbonate. The mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran (1:1), washed with water and dried over magnesium sulfate. The solvent was concentrated under reduced pressure and the residue was triturated with isopropyl ether. The precipitates were collected by filtration, washed with isopropyl ether and dried in vacuo to give 2-acetylamino-5-chloro-4-hydroxymethylthiazole (7.3 g, yield : 78.5%). mp: 145°-146° C. IR (Nujol) : 3150, 1690, 1550, 1285 cm-1

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. additionthe residue was added the aqueous sodium bicarbonate
3. extractionThe mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran (1:1)
4. washwashed with water
5. dry with materialdried over magnesium sulfate
6. concentrationThe solvent was concentrated under reduced pressure
7. customthe residue was triturated with isopropyl ether
8. filtrationThe precipitates were collected by filtration
9. washwashed with isopropyl ether
10. customdried in vacuo

ORD record

ord-f2909747712545b5be30f6c15e0ef389

Source dataset

uspto-grants-1993_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05256675