Benzyl mercaptan → HCID 20475694, compound

Reaction equation

Cl[C:2]1[N:7]=[C:6]([CH3:8])[C:5]([Br:9])=[C:4]([CH3:10])[N:3]=1.[CH:11]1[CH:16]=[CH:15][C:14]([CH2:17][SH:18])=[CH:13][CH:12]=1.CC[O-].[Na+]>C(O)C>[CH2:17]([S:18][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([Br:9])=[C:4]([CH3:10])[N:3]=1)[C:14]1[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=1

Participants

Procedure

2-Chloro-4,6-dimethyl-5-bromopyrimidine (10 mmol) was added to a solution of benzylthiol (11 mmol) and 0.138 M NaOEt in ethanol (80 ml). The mixture was stirred at room temperature for 70 min and then heated under reflux for 40 min. The solvent was then distilled off, the residue extracted with chloroform (50 ml), the chloroform solution washed with 2 M NaOH and the dried (MgSO4) solution evaporated to leave the sulfide which was purified by distillation; yield 94%, b.p. 232°-234° C./15 mmHg. 1H NMR (Cl3CF): δ2.50 (Me-4, Me-6), 4.26 (CH2), 7.20 (Ph).