Acetyl chloride → N-[3-(9-Acetyl-3-oxo-2,3-dihydrocyclopenta[c]carbazol-6(1H)-yl)propyl]-2-nitro-N-propylbenzenesulfonamide
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]([CH2:17][CH2:18][CH2:19][N:20]1[C:32]2[CH:31]=[CH:30][C:29]3[C:33](=[O:36])[CH2:34][CH2:35][C:28]=3[C:27]=2[C:26]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]1=2)[CH2:14][CH2:15][CH3:16])(=[O:12])=[O:11])([O-:3])=[O:2].[Al+3].[Cl-].[Cl-].[Cl-].[C:41](Cl)([CH3:43])=[O:42]>C1([N+]([O-])=O)C=CC=CC=1.O>[C:41]([C:24]1[CH:23]=[CH:22][C:21]2[N:20]([CH2:19][CH2:18][CH2:17][N:13]([CH2:14][CH2:15][CH3:16])[S:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N+:1]([O-:3])=[O:2])(=[O:11])=[O:12])[C:32]3[CH:31]=[CH:30][C:29]4[C:33](=[O:36])[CH2:34][CH2:35][C:28]=4[C:27]=3[C:26]=2[CH:25]=1)(=[O:42])[CH3:43]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
Compound 47 (0.638 g, 1.26 mmol) was dissolved in PhNO2 (7 mL). The solution was cooled on an ice bath, AlCl3 (0.67 g, 5.02 mmol) and then AcCl (0.45 mL, 6.31 mmol) were added. The mixture was kept for 40 min (LC/MS monitoring), diluted with water. The product was extracted with CH2Cl2. The extract was evaporated. The residue was evaporated, and the product was passed through Celite, eluent: CH2Cl2-ethyl acetate 100:0→50:50. Yield of 48: 0.453 g (66%).
Workup
- temperatureThe solution was cooled on an ice bath
- extractionThe product was extracted with CH2Cl2
- customThe extract was evaporated
- customThe residue was evaporated
Sources & evidence
- ORD record
- ord-09cda3e5fda348ef8e38fc79d25da662
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08765738B2
Reaction notes
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