Hydrochloric Acid → HCID 19822112, compound

A solution of triphenylphosphine (2.35 g, 9 mmol) in anhydrous tetrahydrofuran (30 ml) was treated dropwise with diethyl azodicarboxylate (1.4 ml, 9 mmol) over 5 min at 0° C. The solution was stirred at this temperature for 30 min and ten treated with a solution of 2-hydroxy-2,N-dimethyl-1-(pyrid-3-yl)cyclohexane carbothioamide (1.59 g, 6 mmol) in anhydrous tetrahydrofuran (15 ml). The mixture was warmed to room temperature and stirred for 16 h. The solution was then poured into aqueous hydrochloric acid (0.5 M, 60 ml) and extracted with ethyl acetate (3×45 ml). The aqueous phase was basified with 2 M aqueous sodium carbonate solution and extracted with dichloromethane (3×45 ml). The organic extract was dried over magnesium sulphate and evaporated to give a pale brown oil This was subjected to flash chromatography over silica gel, eluting with ethyl acetate/methanol (98:2) to give (±)-2-methylene-N-methyl-1-(pyrid-3-yl)cyclohexane carbothioamide (0.25 g) as a colourless solid, m.p. 106.5°-108.5° C.;

1. stirringstirred for 16 h
2. extractionextracted with ethyl acetate (3×45 ml)
3. extractionextracted with dichloromethane (3×45 ml)
4. extractionThe organic extract
5. dry with materialwas dried over magnesium sulphate
6. customevaporated
7. customto give a pale brown oil
8. washeluting with ethyl acetate/methanol (98:2)

ORD record

ord-a242354996114a0ca555bdf6189720da

Source dataset

uspto-grants-1992_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05104883