Epichlorohydrin → 2-(2-Hydroxy-3-chloropropyl)thio-5-chloropyrimidine

Participants

Reaction Steps

A mixture of 5-chloropyrimidine-2-thione (14 mmol) and triethylamine (14 mmol) was stirred together in dichloromethane (30 ml) for 5 min before epichlorohydrin (15 mmol) was added. The mixture was stirred at room temperature for 3 h, the solvent evaporated, the residue triturated with water, the insoluble material extracted with chloroform, the dried (MgSO4) chloroform solution evaporated and the residue crystallized from chloroform:pet. ether; yield 30%, m.p. 99° C. 1H NMR (acetone-d6): δ3.3-3.8 (2CH2, m) 3.9-4.4 (CH, m), 4.6-4.7 (OH), 8.59 (H-4, H-6).

Provenance & Evidence