Potassium Carbonate → 2-(7-Chloroquinolin-2-yl)methoxy-11-(3-ethoxycarbonylpropylthio)-6,11-dihydrodibenz[b,e]oxepine

HRID 232847Notes

Reaction equation

HRID 232847 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[CH:13][C:14]([CH2:18][O:19][C:20]3[CH:35]=[CH:34][C:23]4[O:24][CH2:25][C:26]5[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=5[CH:28]([SH:29])[C:22]=4[CH:21]=3)=[N:15]2)=[CH:10][CH:9]=1.Br[CH2:37][CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41]>CC(C)=O>[Cl:7][C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[CH:13][C:14]([CH2:18][O:19][C:20]3[CH:35]=[CH:34][C:23]4[O:24][CH2:25][C:26]5[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=5[CH:28]([S:29][CH2:37][CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])[C:22]=4[CH:21]=3)=[N:15]2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 233591992-(7-Chloroquinolin-2-yl)methoxy-11-mercapto-6,11-dihydrodibenz[b,e]oxepine

Product 1

HCID 233591262-(7-Chloroquinolin-2-yl)methoxy-11-(3-ethoxycarbonylpropylthio)-6,11-dihydrodibenz[b,e]oxepineYield 67.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

0.43 g of potassium carbonate was added to 1 g of 2-(7-chloroquinolin-2-yl)methoxy-11-mercapto-6,11-dihydrodibenz[b,e]oxepine and 0.56 g of ethyl 4-bromobutanoate dissolved in 25 ml of acetone and the mixture was stirred under heating for 3 hours. After completion of the reaction, the reaction mixture was filtered and the filtrate was condensed under reduced pressure. The resulting residue was applied to silica gel column chromatography to obtain 0.86 g of 2-(7-chloroquinolin-2-yl)methoxy-11-(3-ethoxycarbonylpropylthio)-6,11-dihydrodibenz[b,e]oxepine as a brown oily product.

Workup

  1. temperatureunder heating for 3 hours
  2. customAfter completion of the reaction
  3. filtrationthe reaction mixture was filtered
  4. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-cee62b149fc849b294935b46a407723b
Source dataset
uspto-grants-1997_01
Patent number
US05591752

Reaction notes

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