1,3-Dichloroacetone → 4-Thiazolol, 4-(chloromethyl)-2-[(dimethylamino)methyl]-4,5-dihydro-

To a flask were added 44.5 g. of dimethylaminothioacetamide, hydrochloride, 40.4 g. of 1,3-dichloropropanone, 224 ml. of 1,2-dichloroethane and 53.4 g. of sodium bicarbonate. An endothermic reaction took place and cooled the mixture to 13° on initial mixing. The mixture was then stirred overnight at ambient temperature, and the reaction was found to be essentially complete after 24 hours, by thin layer chromatography. The tlc system is silica gel, eluting with chloroform:methanol:ammonium hydroxide, 36:4:1. The mixture was then filtered, and the filter cake was washed with 1,2-dichloroethane. The filtrate was evaporated to dryness under vacuum to obtain 59.5 g. of crude product, which was washed with ethyl acetate. The washed solids were dried in air, to obtain 52.5 g. of substantially pure product, m.p. 90°-92°.

1. additionTo a flask were added 44.5 g
2. customAn endothermic reaction
3. temperaturecooled the mixture to 13°
4. additionon initial mixing
5. waitto be essentially complete after 24 hours, by thin layer chromatography
6. washeluting with chloroform
7. filtrationThe mixture was then filtered
8. washthe filter cake was washed with 1,2-dichloroethane
9. customThe filtrate was evaporated to dryness under vacuum
10. customto obtain 59.5 g
11. washof crude product, which was washed with ethyl acetate
12. customThe washed solids were dried in air
13. customto obtain 52.5 g

ORD record

ord-e8bd3693e1b94ece8f8e0f2ef01e9c4b

Source dataset

uspto-grants-1984_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04468517