ClC1C(Cl)=C([OH:9])C(Cl)=C(Cl)N=1.[C:12]([O:16][CH2:17][CH2:18][N:19]=[C:20]=[O:21])(=[O:15])[CH2:13][CH3:14].CC(C)=O.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC.CCCCCC>[O:15]=[C:12]([O:16][CH2:17][CH2:18][NH:19][C:20](=[O:9])[OH:21])[CH2:13][CH3:14]
11.7 Grams of 2,3,5,6-tetrachloro-4-pyridinol, 7.2 grams of isocyanatoethyl propionate, and a few drops of dibutyltin dilaurate (as activating agent) were added to 200 ml of acetone and stirred at reflux temperature for eight hours and then allowed to stand. The mixture was again stirred at reflux temperature for an additional seven hours before the addition of 6.0 grams of potassium carbonate. The reactants were then stirred for another hour after which the insoluble components were filtered off and the solvent removed under reduced pressure, leaving a residue. The resulting residue was slurried in n-hexane, cooled, and filtered to yield about 15 grams of soft, white solid as the desired 2,3,5,6-tetrachloro-4-pyridinyl ester of (2-(1-oxopropoxy)ethyl)carbamic acid.
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