(Chlorothio)formyl chloride → 5-(4-Chloro-2-methoxyphenyl)-1,3,4-oxathiazol-2-one
Reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1.Cl[C:14]([S:16]Cl)=[O:15]>O1CCCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[O:7][C:14](=[O:15])[S:16][N:8]=2)=[C:4]([O:11][CH3:12])[CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
In tetrahydrofuran (100 ml), 4-chloro-2-methoxybenzamide (5.67 g, 30.5 mmol) prepared in the Step 7-1-1 and chlorocarbonylsulfenyl chloride (4.40 g, 33.6 mmol) were suspended, and the mixture was heated under reflux for 1.5 hours. After being allowed to cool, the mixture was subjected to extraction with ethyl acetate, and the extract was dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (n-hexane:ethyl acetate=7:1) to give the title compound (5.33 g, 71%).