Hydracrylonitrile → 2-(7-Chloroquinolin-2-yl)methoxy-11-(2-cyanoethoxy)-6,11-dihydrodibenz[b,e]oxepine

HRID 232880Notes

Reaction equation

HRID 232880 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][C:12]([CH2:16][O:17][C:18]3[CH:33]=[CH:32][C:21]4[O:22][CH2:23][C:24]5[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=5[CH:26]([OH:27])[C:20]=4[CH:19]=3)=[N:13]2)=[CH:8][CH:7]=1.[CH2:34]([C:37]#[N:38])[CH2:35]O.C(N(CC)CC)C>C(Cl)Cl>[Cl:5][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][C:12]([CH2:16][O:17][C:18]3[CH:33]=[CH:32][C:21]4[O:22][CH2:23][C:24]5[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=5[CH:26]([O:27][CH2:35][CH2:34][C:37]#[N:38])[C:20]=4[CH:19]=3)=[N:13]2)=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 8011HydracrylonitrileHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 233591192-(7-Chloroquinolin-2-yl)methoxy-11-hydroxy-6,11-dihydrodibenz[b,e]oxepine

Product 1

HCID 233592112-(7-Chloroquinolin-2-yl)methoxy-11-(2-cyanoethoxy)-6,11-dihydrodibenz[b,e]oxepine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under ice cooling and stirring, 0.27 ml of thionyl chloride was added 1.5 g of 2-(7-chloroquinolin-2-yl)methoxy-11-hydroxy-6,11-dihydrodibenz[b,e]oxepine obtained in Reference example 36 suspended in 30 ml of methylene chloride and the mixture was stirred at the same temperature for 40 minutes. After completion of the reaction, the reaction mixture was condensed under reduced pressure, the residue was dissolved in 12 ml of methylene chloride, 0.81 ml of ethylenecyanhydrin and 0.94 ml of triethylamine were added to the solution under ice cooling and stirring and the mixture was stirred at room temperature for 2.5 hours. The reaction mixture was washed with water and the organic layer was dried over anhydrous sodium sulfate. Solid obtained by removing the solvent was washed with a diethyl ether-hexane mixed solution to obtain 1.31 g of the title compound.

Workup

  1. customobtained in Reference example 36
  2. stirringthe mixture was stirred at the same temperature for 40 minutes
  3. customAfter completion of the reaction
  4. customcondensed under reduced pressure
  5. stirringstirring
  6. stirringthe mixture was stirred at room temperature for 2.5 hours
  7. washThe reaction mixture was washed with water
  8. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  9. customSolid obtained
  10. customby removing the solvent
  11. washwas washed with a diethyl ether-hexane mixed solution

Sources & evidence

ORD record
ord-32633080cc164b10bd5fca74d30a8f21
Source dataset
uspto-grants-1997_01
Patent number
US05591752

Reaction notes

Loading…