[CH2:1]([O:3][C:4]([SH:6])=[S:5])[CH3:2].[K].[C:8]([C:11]1[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=1[N+]#N)([OH:10])=[O:9].[B-](F)(F)(F)F>CC(C)=O>[Cl:17][C:16]1[C:11]([C:8]([OH:10])=[O:9])=[C:12]([S:5][C:4]([O:3][CH2:1][CH3:2])=[S:6])[CH:13]=[CH:14][CH:15]=1To a stirred suspension of 2.4 grams (0.014 mole) of ethylxanthic acid, potassium salt in 30 mL of acetone was added, by pipette, a stirred suspension of 2.0 grams (0.007 mole) of 2-carboxy-3-chlorobenzenediazonium tetrafluoborate in 50 mL of acetone. The flask containing the fluoborate suspension was rinsed with 20 mL of acetone, and the rinse was added to the reaction mixture. Upon completion of addition which required 7 minutes, the reaction mixture was stirred for about 18 hours. The reaction mixture was filtered to collect 2.0 grams of 6-chloro-2-[ethoxy(thiocarbonyl)thio]benzoic acid. The nmr spectrum was consistent with the proposed structure.
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