C([N:3]([CH2:6][CH3:7])[CH2:4]C)C.[C-:8]1(C(O)=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9]1.[CH-:16]1[CH:20]=[CH:19]C=C1.[Fe+2:21].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[C:39]([O:43][CH2:44][CH3:45])(=[O:42])[NH:40][NH2:41]>ClCCl.C1(C)C=CC=CC=1>[C-:6]1([NH:3][C:4]([NH:41][NH:40][C:39]([O:43][CH2:44][CH3:45])=[O:42])=[O:14])[CH:7]=[CH:19][CH:20]=[CH:16]1.[CH-:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1.[Fe+2:21]Under ice cooling, 0.6 mL (4.3 mmols) of triethylamine was added to a mixture of 0.5 g (2.17 mmols) of ferrocenecarboxylic acid (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 0.47 mL (2.17 mmols) of diphenylphosphorylazide and 4 mL of toluene and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was diluted with dichloromethane. The dilution was washed sequentially with a 1% hydrochloric acid aqueous solution and saturated sodium hydrogencarbonate solution. After drying over anhydrous magnesium sulfate, the organic layer was filtered and concentrated under reduced pressure to give 4 mL of the toluene solution. To the toluene solution obtained, 2 mL of toluene was added and 0.34 g (3.27 mmols) of ethyl carbazate was added to the mixture while stirring at room temperature. The reaction mixture was heated under reflux for an hour and then diluted with dichloromethane. The dilution was washed sequentially with a 1% hydrochloric acid aqueous solution and saturated sodium hydrogencarbonate solution. After drying over anhydrous magnesium sulfate, the organic layer was filtered and then concentrated under reduced pressure. The resulting residue was washed with a hexane-dichloromethane (1:1) mixture to give 0.52 g (72%) of ethyl 3-ferrocenylcarbamoylcarbazate as yellow powders.
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