ClS([N:5]=[C:6]=[O:7])(=O)=O.[CH3:8][C:9]1([CH3:16])[CH2:14][CH2:13][C:12](=[CH2:15])[CH2:11][CH2:10]1.O.O.O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+].[OH-].[K+]>C(OCC)C>[CH3:8][C:9]1([CH3:16])[CH2:14][CH2:13][C:12]2([NH:5][C:6](=[O:7])[CH2:15]2)[CH2:11][CH2:10]1
Chlorosulfonyl isocyanic acid (0.67 mL, 7.7 mmol) was dropped into the dehydrated diethyl ether (11 mL) solution of 1,1-dimethyl-4-methylene-cyclohexane (0.91 g, 7.4 mmol), which had been obtained in 1), in an ice bath. The reaction mixture was stirred at room temperature for 1 hour, and chlorosulfonyl isocyanic acid (0.67 mL, 7.7 mmol) was added in the reaction required in the ice bath and further stirred at room temperature for 1 hour. After chlorosulfonyl isocyanic acid (0.32 mL, 3.7 mmol) had been added in the reaction mixture in the ice bath and further stirred at room temperature for 2 hours, the aqueous solution (4.5 mL) containing sodium thiosulfate pentahydrate (4.56 g, 18.4 mmol) and 10% potassium hydroxide solution was added alternately in the reaction mixture in the ice bath and the pH was adjusted to be about 10, and then the reaction mixture was stirred for 2 hours. The insoluble matter was removed by filtration, and the filtrate was extracted with chloroform. Then the organic layer was washed with water and dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure and a colorless solid (0.75 g) was obtained.
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