[CH3:1][NH:2][C:3](=[O:15])[O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1.N1C=CC=CC=1.[S:22](Cl)(Cl)=O.[C:26]1([SH:32])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O1CCCC1>[CH3:1][N:2]([S:32]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[S:22])[C:3](=[O:15])[O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1To a solution of 1-naphthyl methylcarbamate (4.0 g, 0.02 mol) in 20 ml dry tetrahydrofuran was added 1.9 g pyridine (0.024 mol) and 2.5 g thionyl chloride (0.021 mol). The mixture was stirred at room temperature for 6 hours. The reaction mixture was cooled in an ice-water bath and 1.9 g pyridine was added followed by 2.2 g benzenethiol (0.02 mol) added dropwise. Stirring was continued for an additional 1 hour and the mixture was worked up in the usual manner as previously described in Example I. A sample was purified by preparative thin-layer chromatography. Nmr spectrum of the pure product in chloroform-d-TMS showed the following absorptions: δ 8.1-6.9 (m, 12H, aromatic protons), 3.2 (s, 3H, NCH3).
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