Sodium Hydroxide → 2-(7-Chloroquinolin-2-yl)methoxy-11-(2-cyanoethylthio)-6,11-dihydrodibenz[b,e]oxepine
Reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]([CH2:9][CH2:10][S:11][CH:12]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH2:16][O:15][C:14]2[CH:23]=[CH:24][C:25]([O:27][CH2:28][C:29]3[CH:38]=[CH:37][C:36]4[C:31](=[CH:32][C:33]([Cl:39])=[CH:34][CH:35]=4)[N:30]=3)=[CH:26][C:13]1=2)(=O)[NH2:7].[OH-].[Na+]>CN(C)C=O>[Cl:39][C:33]1[CH:32]=[C:31]2[C:36]([CH:37]=[CH:38][C:29]([CH2:28][O:27][C:25]3[CH:24]=[CH:23][C:14]4[O:15][CH2:16][C:17]5[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=5[CH:12]([S:11][CH2:10][CH2:9][C:6]#[N:7])[C:13]=4[CH:26]=3)=[N:30]2)=[CH:35][CH:34]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Under ice cooling and stirring, 1.35 ml of phosphorus oxy-chloride was added dropwise over 40 minutes to 1.78 g of 11-(2-carbamoylethylthio)-2-(7-chloroquinolin-2-yl)methoxy-6,11-dihydrodibenz[b,e]oxepine obtained in Reference example 63 dissolved in 14 ml of dimethylformamide and the mixture was stirred at the same temperature for 30 minutes. The reaction mixture was added 250 ml of a 1% sodium hydroxide aqueous solution, crystals precipitated were collected by filtration and the crystals were dissolved in chloroform. After this chloroform solution was washed with water and dried over anhydrous sodium sulfate, the solvent was removed to obtain 1.62 g of the title compound.
Workup
- customobtained in Reference example 63
- stirringthe mixture was stirred at the same temperature for 30 minutes
- customprecipitated
- filtrationwere collected by filtration
- dissolutionthe crystals were dissolved in chloroform
- washAfter this chloroform solution was washed with water
- dry with materialdried over anhydrous sodium sulfate
- customthe solvent was removed
Sources & evidence
- ORD record
- ord-6a5a64fb2f7e44cf90fd5061572d66b0
- Source dataset
- uspto-grants-1997_01
- Patent number
- US05591752
Reaction notes
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