Ammonia → 11-(2-Carbamoylethylthio)-2-(7-chloroquinolin-2-yl)methoxy-6,11-dihydrodibenz[b,e]oxepine

HRID 232878Notes

Reaction equation

HRID 232878 reaction equation
C(N1C=CN=C1)([N:3]1C=CN=C1)=O.[C:13]([CH2:16][CH2:17][S:18][CH:19]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[CH2:23][O:22][C:21]2[CH:30]=[CH:31][C:32]([O:34][CH2:35][C:36]3[CH:45]=[CH:44][C:43]4[C:38](=[CH:39][C:40]([Cl:46])=[CH:41][CH:42]=4)[N:37]=3)=[CH:33][C:20]1=2)(O)=[O:14].N.O>O1CCCC1>[C:13]([CH2:16][CH2:17][S:18][CH:19]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[CH2:23][O:22][C:21]2[CH:30]=[CH:31][C:32]([O:34][CH2:35][C:36]3[CH:45]=[CH:44][C:43]4[C:38](=[CH:39][C:40]([Cl:46])=[CH:41][CH:42]=4)[N:37]=3)=[CH:33][C:20]1=2)(=[O:14])[NH2:3]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 2335913211-(2-Carboxyethylthio)-2-(7-chloroquinolin-2-yl)methoxy-6,11-dihydrodibenz[b,e]oxepine

Product 1

HCID 2335915311-(2-Carbamoylethylthio)-2-(7-chloroquinolin-2-yl)methoxy-6,11-dihydrodibenz[b,e]oxepineYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.98 g of 1,1'-carbonyldiimidazole was added to 1.99 g of 11-(2-carboxyethylthio)-2-(7-chloroquinolin-2-yl)methoxy-6,11-dihydrodibenz[b,e]oxepine obtained in Example 2 dissolved in 33 ml of tetrahydrofuran and the mixture was stirred at room temperature for 4 hours. Then, 4 ml of conc. aqueous ammonia was added to the mixture and the mixture was stirred at room temperature for 10 minutes. The reaction mixture was condensed under reduced pressure, water was added to the residue, crystals 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, solid obtained by removing the solvent was washed with an acetone-hexane mixed solution to obtain 1.99 g of the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature for 10 minutes
  2. additionwas added to the residue, crystals
  3. filtrationwere collected by filtration
  4. dissolutionthe crystals were dissolved in chloroform
  5. washAfter this chloroform solution was washed with water
  6. dry with materialdried over anhydrous sodium sulfate, solid
  7. customobtained
  8. customby removing the solvent
  9. washwas washed with an acetone-hexane mixed solution

Sources & evidence

ORD record
ord-d1b0a40a3a2247f39bee7bbdf9c8dcdd
Source dataset
uspto-grants-1997_01
Patent number
US05591752

Reaction notes

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