[Cl:1][C:2]1[C:3]([C:9]([OH:11])=[O:10])=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[OH-].[Na+].C1COCC1.CN([CH:22]([SH:24])C)C.[CH3:25][N:26]([CH:28]=O)[CH3:27]>O>[Cl-:1].[C:9]([C:3]1[N:4]=[C:5]([S:24][CH2:22][CH2:28][NH+:26]([CH3:27])[CH3:25])[CH:6]=[CH:7][C:2]=1[Cl:1])([OH:11])=[O:10]
3,6-Dichloropyridine-2-carboxylic acid (1.0 g, 5.23 mmol.), sodium hydroxide (1.64 g, 15.7 mmol.), and anhydrous THF (10 mL) were combined before slowly adding the N,N-dimethylaminoethanethiol (1.9 g, 18.3 mmol). After stirring for several hours under nitrogen, two aliquots of DMF (10 mL each) were added. Several hours later, additional DMF (10 mL) and dimethylaminoethanethiol (1.9 g, 18.3 mmol) were added. The reaction was stirred overnight at room temperature. The solution was diluted with water and extracted three times with methylene chloride. The aqueous was acidified to pH 5 and extracted four times with methylene chloride. The aqueous was acidified to pH 1, the solvent was removed, and the residue was recrystallized from hot water. Yellow solid, 0.786 g (51% yield). 1H NMR (300 MHz, CD3OD): δ 2.98 (s, 6H), 3.53 (m, 4H), 7.50 (d, 1H), 7.85 (d, 1H). 13C NMR (75 MHz, CD3OD): δ 24.4, 42.8, 58.2, 125.7, 128.1, 140.0, 147.3, 158.2, 166.0.
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