反应详情

A solution of [[[(1,1-dimethylethoxy)carbonyl]amino]-(methylthio)methylene]-carbamic acid, 1,1-dimethylethyl ester [CAS 107819-90-9] (21 g, 0.0723 mol) in DMF (450 mL) was treated sequentially with thiomorpholine (7 mL, 0.0723 mol), mercury chloride (19.6 g, 0.0723 mol), and Et3N (30 mL, 0.22 mol) and the reaction mixture was stirred for 18 h. The mixture was diluted with EtOAc and filtered through a pad of diatomaceous earth. The filtrate was concentrated, diluted with water and EtOAc and filtered again through a pad of diatomaceous earth. The filtrate aqueous layer was separated and extracted with EtOAc (2×). The combined organic layers were washed with water, then satd. aq. NaCl, dried, and concentrated. The solid was triturated with 20% Et2O/40-60° C. petrol. The solid was filtered off and was washed with 20% Et2O/40-60° C. petrol followed by 40-60° C. petrol. The solid was dried under vacuum to give 21.2 g (85%) as a white solid. Note: The reaction was performed with a trap for gaseous loss of methanethiol.

1. filtrationfiltered through a pad of diatomaceous earth
2. concentrationThe filtrate was concentrated
3. additiondiluted with water and EtOAc
4. filtrationfiltered again through a pad of diatomaceous earth
5. customThe filtrate aqueous layer was separated
6. extractionextracted with EtOAc (2×)
7. washThe combined organic layers were washed with water
8. dry with materialaq. NaCl, dried
9. concentrationconcentrated
10. customThe solid was triturated with 20% Et2O/40-60° C. petrol
11. filtrationThe solid was filtered off
12. washwas washed with 20% Et2O/40-60° C. petrol
13. customfollowed by 40-60° C.
14. customThe solid was dried under vacuum
15. customto give 21.2 g (85%) as a white solid