[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][SH:10])=[CH:7][CH:6]=1.[C:13](#[N:17])[CH2:14][C:15]#[N:16]>C(O)C.O.[NH4+].[Cl-].O>[CH3:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][S:10][C:13](=[NH:17])[CH2:14][C:15]#[N:16])=[CH:7][CH:6]=1
To a solution of sodium hydroxide (13 g, 0.32 mol) in 750 mL of 1:1 ethanol-water at 0° C. was added 4-methoxybenzylmercaptan (50 g, 0.324 mol) and malononitrile (21 g, 0.324 mol). After stirring for 3 hours at 0° C., the mixture was diluted with 500 mL of saturated aqueous NH4Cl, diluted with 4 l of water and filtered. The solids were washed with ether, and the filtrated was diluted with an equal volume of hexane and filtered. The combined solids were dried in vacuo, affording 43 g (60%) of 2-cyano-thioacetimidic acid 4-methoxy-benzyl ester as a colorless solid. 1H NMR (400 MHz, CDCl3) δ 7.22 (d, 2H, J=7.6 Hz), 6.84 (d, 2H, J=8.8 Hz), 4.74 (bs, 1H), 3.98 (s, 2H), 3.78 (s, 3H) ppm; MS (APCl, m/z): 221 [M+H]+.
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