O[C:2]1[CH:16]=[CH:15][C:5]2[N:6](C3C=CC=CC=3)[CH:7]=[N:8][C:4]=2[CH:3]=1.C1COCC1.[CH3:22][N:23]([CH:25]=[O:26])[CH3:24].[H-].[Na+].CN(C)C(Cl)=[S:32]>C1COCC1>[CH3:22][N:23]([CH3:24])[C:25](=[S:32])[O:26][C:7]1[NH:8][C:4]2[CH:3]=[CH:2][CH:16]=[CH:15][C:5]=2[N:6]=1A solution of 5-hydroxy-1-phenylbenzimidazole (Example 14) (0.88 g, 4.10 mmol) in 1:1 THF/DMF (15 mL) was added dropwise under nitrogen to a stirred suspension of NaH (0.24 g of a 50% dispersion in oil, 5.00 mmol) in THF (10 mL). After 10 minutes a solution of dimethylthiocarbamyl chloride (0.57 g, 4.6 mmol) in THF (5 mL) was added and the solution was warmed at 60° C. for 1 hour. The cooled solution was partitioned between ether and 2N KOH and the organic portion was worked up and chromatographed on silica. Elution with EtOAc/petroleum ether (7:3) gave the O-benzimidazolyl dimethylthiocarbamate (0.76 g, 65%), mp (EtOAc/petroleum ether) 173-174.5° C.
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