[CH3:1][O-].[Na+].[N:4]#[C:5][NH2:6].[Cl:7][C:8]1[CH:15]=[C:14]([N:16]=[C:17]=[S:18])[CH:13]=[C:12]([Cl:19])[C:9]=1[C:10]#[N:11].CI>CO>[C:5](/[N:6]=[C:17](\[S:18][CH3:1])/[NH:16][C:14]1[CH:15]=[C:8]([Cl:7])[C:9]([C:10]#[N:11])=[C:12]([Cl:19])[CH:13]=1)#[N:4]Sodium methoxide (0.5M in methanol) (5.7 ml, 2.85 mmol, Eq: 1.22) was added to cyanamide (108 mg, 2.58 mmol, Eq: 1.1). After 15 minutes, the solution was added to a solution of 2,6-dichloro-4-isothiocyanatobenzonitrile (537 mg, 2.34 mmol, Eq: 1.00) in methanol (5 mL). After 1 hr, methyl iodide (704 mg, 310 μl, 4.96 mmol, Eq: 2.11) was added and the reaction was stirred overnight at room temperature. The resulting suspension was filtered and dried to give 43 mg of desired product as a gray solid. The filtrate was concentrated and chromatographed (40 g Analogix, 50% EtOAc/hex to 75% EtOAc/hex) to give 191 mg of desired product as a yellow solid. The solids were combined to give 234 mg (35%) of desired product.
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