2-Chlorocyclopentanone → 2-acetoxymethyl-5,6-dihydro-4H-cyclopentathiazole

Temperature

80 °C

A mixture of 2-acetoxythioacetamide (10 g), 2-chlorocyclopentanone (10.6 g) and dimethylformamide (100 ml) was stirred for 24 hours at 80° C. The reaction mixture was cooled and poured into ice-water (500 ml), followed by extraction twice with ethyl acetate (200 ml). The extract was washed twice with water (100 ml), which was dried over magnesium sulfate, then the solvent was distilled off under reduced pressure. The residue was subjected to a silica gel chromatography (2.5×50 cm), eluting with ethyl acetate-hexane (3:7). The object fraction was concentrated to give 2-acetoxymethyl-5,6-dihydro-4H-cyclopentathiazole (5 g) as a yellow oily product.

1. temperatureThe reaction mixture was cooled
2. extractionfollowed by extraction twice with ethyl acetate (200 ml)
3. washThe extract was washed twice with water (100 ml), which
4. dry with materialwas dried over magnesium sulfate
5. distillationthe solvent was distilled off under reduced pressure
6. washeluting with ethyl acetate-hexane (3:7)
7. concentrationThe object fraction was concentrated

ORD record

ord-688df7a317ff428e8eb86212c13c335c

Source dataset

uspto-grants-1995_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05405861