Cl[C:2]1SC2C(O)=C(C(OC)=O)N(C)S(=O)(=O)C=2C=1.NC1C=CC=CN=1.[Cl:26][C:27]1[S:31][C:30]([C:32]([OH:34])=[O:33])=[C:29]([S:35](=[O:39])(=[O:38])[NH:36][CH3:37])[CH:28]=1.C.ClC1SC2C(O)=C(C(=O)NC3C=CC=CN=3)N(C)S(=O)(=O)C=2C=1>OCC(CO)O.C1(C)C(C)=CC=CC=1>[Cl:26][C:27]1[S:31][C:30]([C:32]([O:34][CH3:2])=[O:33])=[C:29]([S:35](=[O:38])(=[O:39])[NH:36][CH3:37])[CH:28]=11200 ml. of absolute xylene are placed in a 2 liter volume flask and 11 g. of 6-chloro-4-hydroxy-2-methyl-3-methoxycarbonyl-2H-thieno[2,3-e]-1,2-thiazine-1,1-dioxide are added while stirring. 4.42 g. of 2-aminopyridine are next added and the solution is then boiled under reflux until all the starting product has been shown by thin layer chromatography to have reacted (about 4 hours). A gentle stream of nitrogen is passed through the mixture during boiling under reflux, in order to entrain the methanol that is formed. After the end of the reaction, the solution is cooled to about 120°, activated charcoal is added, and the solution is boiled for an additional short time. A hot water funnel is filled with glycerol and preheated to 120°, and the hot reaction solution at 120° is then filtered through this funnel. When the temperature of the solution has fallen to 70°, the solution is then scratched, whereupon small orange crystals begin to separate out. When cold, the solution is kept for 12 hours in an icebox (-5°) and the precipitate that has separated out is filtered under suction and washed with xylene. The product is dried in vacuo (1 mm, 120°, 2 hours). The orange to yellow crystals thus obtained are 6-chloro-4-hydroxy-2-methyl-3-(2-pyridylcarbamoyl)-2H-thieno[2,3-e]-1,2-thiazine-1,1-dioxide with a melting point of 225°-230° (with decomposition).
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