Thionyl Chloride → 3-(6,11-Dihydro-11-oxodibenz[b,e]oxepin-2-yl)propanyl chloride

HRID 357252Notes

Reaction equation

HRID 357252 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([CH2:17][CH2:18][C:19](O)=O)=[CH:16][C:3]1=2.S(Cl)([Cl:24])=O>CN(C)C=O.C(Cl)Cl>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][O:5][C:4]2[CH:13]=[CH:14][C:15]([CH2:17][CH2:18][CH2:19][Cl:24])=[CH:16][C:3]1=2

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 123929606,11-Dihydro-11-oxodibenz[b,e]oxepin-2-propanoic acid

Product 1

HCID 677979853-(6,11-Dihydro-11-oxodibenz[b,e]oxepin-2-yl)propanyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a flask was added a few drops of N,N-dimethylformamide and 32.25 g of 3-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)propanoic acid in 500 ml of dry methylene chloride. The chilled stirring suspension was treated dropwise over several minutes with 11.0 ml of thionyl chloride. The suspension was warmed intermittently on a steam bath until all gas evolution ceased. The resulting solution was then allowed to reflux of 15 minutes and was allowed to stand at room temperature under nitrogen atmosphere overnight. The solution was concentrated in vacuo to an oil. The oil was dissolved in 500 ml of methylene chloride and was treated with another 11.0 ml of thionyl chloride. The solution was allowed to reflux for 3 hours and was again concentrated to an oil in vacuo. The oil still contained a significant amount of crystalline impurity, which was filtered away after triturating with a hexane/ether solution the supernatant was concentrated to an oil in vacuo which solidified overnight in refrigeration. The purified solids were recrystallized from three portions of cyclohexene to give 25.03 g of 3-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)propanyl chloride, m.p. 69°-72° C.

Workup

  1. temperatureThe suspension was warmed intermittently on a steam bath until all gas evolution
  2. temperatureto reflux of 15 minutes
  3. concentrationThe solution was concentrated in vacuo to an oil
  4. dissolutionThe oil was dissolved in 500 ml of methylene chloride
  5. additionwas treated with another 11.0 ml of thionyl chloride
  6. temperatureto reflux for 3 hours
  7. concentrationwas again concentrated to an oil in vacuo
  8. filtrationwas filtered away
  9. customafter triturating with a hexane/ether solution the supernatant
  10. concentrationwas concentrated to an oil in vacuo which
  11. waitsolidified overnight in refrigeration
  12. customThe purified solids were recrystallized from three portions of cyclohexene

Sources & evidence

ORD record
ord-783256b23e5b47428f657e028dbb2039
Source dataset
uspto-grants-1998_11
Patent number
US05840749

Reaction notes

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