Methanethiol → Methyl 2-methoxy-6-(methylthio)-nicotinate

Reaction equation

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

Participants

Procedure

To 10 ml of a 1 N methanolic sodium methoxide solution are added dropwise 3 ml of a 3.5 N methanolic methylmercaptan solution. To the resultant methylmercaptide solution is added a solution of 2.01 g (0.01 mole) of methyl 2-methoxy-6-chloronicotinate (cf. Example 6 a)) in 30 ml of methanol. The reaction mixture is refluxed for 5 hours and the solvent is thereafter evaporated in vacuo. The residue is treated with 30 ml of saturated potassium carbonate solution and 150 ml of methylene chloride and separated in a separating funnel. The methylene chloride solution is dried over sodium sulphate and subsequently evaporated to dryness in vacuo. The crystallised residue is recrystallised from pentane and yields the methyl 2-methoxy-6-(methylthio)-nicotinate with a melting point of 71°-75° C.