Water → Dimethyl-sulfamic acid 3-cyano-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazol-8-yl ester
Reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:17](=[O:18])[C:16]3[C:15]4[C:10](=[CH:11][C:12]([C:19]#[N:20])=[CH:13][CH:14]=4)[NH:9][C:8]=3[C:7]([CH3:22])([CH3:21])[C:6]=2[CH:23]=1.[H-].[Na+].[CH3:26][N:27]([CH3:32])[S:28](Cl)(=[O:30])=[O:29].O>CN(C=O)C>[C:19]([C:12]1[CH:11]=[C:10]2[C:15]([C:16]3[C:17](=[O:18])[C:5]4[CH:4]=[CH:3][C:2]([O:1][S:28](=[O:30])(=[O:29])[N:27]([CH3:32])[CH3:26])=[CH:23][C:6]=4[C:7]([CH3:21])([CH3:22])[C:8]=3[NH:9]2)=[CH:14][CH:13]=1)#[N:20]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
8-Hydroxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound A6, 50 mg, 0.165 mmol) was dissolved in DMF (1.5 mL), added with sodium hydride (13 mg, 2.0 eq.) and dimethylsulfamoyl chloride (0.02 mL, 1.2 eq.), and then stirred at room temperature for 1 hr. Water was added to the reaction solution, which was then extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. The drying agent was removed by filtration and the residues were concentrated under reduced pressure to obtain the target compound (yellowish white powder, 62 mg, 92%).
Workup
- extractionwas then extracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over sodium sulfate
- customThe drying agent was removed by filtration
- concentrationthe residues were concentrated under reduced pressure
- customto obtain the target compound (yellowish white powder, 62 mg, 92%)
Sources & evidence
- ORD record
- ord-eb0ab39f44144ac3991d9a8e7f9089bc
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09440922B2
Reaction notes
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