alpha,4-Dichloroanisole → 2-(4-Chlorophenoxymethyl)thio-5-chloropyrimidine

Participants

Reaction Steps

A mixture of p-chlorophenoxymethyl chloride (6 mmol) and the potassium salt of 5-chloropyrimidine-2-thione (5 mmol) in 1,2-dimethoxyethane (25 ml) was stirred at room temperature for 10 h, the solvent distilled off at reduced pressure, the residue extracted with chloroform (70 ml), the chloroform (70 ml), the chloroform solution washed with 1 M NaOH (2×10 ml) and water (10 ml), and the dried (MgSO4) solution evaporated. The residual sulfide was recrystallized from iPrOH; yield 70%, m.p. 120° C. 1H NMR (DMSO-d6): δ5.90 (SCH2), 6.98 and 7.31 (Ph), 8.78 (H-4, H-6).

Provenance & Evidence