[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:24])[CH:5]([C:12](=[O:23])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][Cl:22])=[CH:15][CH:14]=1)[C:6]2=[O:11].[N+](C1C=CC([O:34][C:35](=O)[NH:36][N:37]2[CH2:42][CH2:41][O:40][CH2:39][CH2:38]2)=CC=1)([O-])=O>CC#N.CN(C)C1C=CN=CC=1>[Cl:22][CH2:21][CH2:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]([CH:5]2[C:4](=[O:24])[C:3]3[C:7](=[CH:8][CH:9]=[CH:10][C:2]=3[NH:1][C:35]([NH:36][N:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)=[O:34])[C:6]2=[O:11])=[O:23])=[CH:14][CH:15]=1To a suspension of 4-amino-2-[4-(2-chloroethoxy)benzoyl]indan-1,3-dione (36 g, 105 mmol) in CH3CN (600 mL) was added morpholin-4-ylcarbamic acid 4-nitrophenyl ester (40 g, 120 mmol) followed by 4-dimethylaminopyridine (640 mg, 5.2 mmol). The reaction was heated at reflux for 4 hours then cooled to room temp. and stirred overnight. The bright yellow solid is collected by filtration, rinsed with Et2O and dried under vacuum to give the desired semicarbazide (40.5 g, 82% yield).
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