Dichloromethane → HCID 14724117, compound

HRID 1639126Notes

Reaction equation

HRID 1639126 reaction equation
[OH:1][CH: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]([C:17]([O:19][CH3:20])=[O:18])=[CH:16][C:3]1=2.S(Cl)(Cl)=O.[CH2:25](Cl)Cl>>[CH3:25][O:1][CH: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]([C:17]([O:19][CH3:20])=[O:18])=[CH:16][C:3]1=2

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 2769059Methyl 11-hydroxy-6,11-dihydrobenzo[c][1]benzoxepine-2-carboxylate

Product 1

HCID 14724117HCID 14724117, compound

Procedure

In 300 ml of methylene chloride was dissolved 30.0 g of Compound b obtained in Reference Example 2. Under ice cooling, 10 ml of thionyl chloride was dropwise added to the solution. After stirring for further 2 hours under ice cooling, the reaction mixture was concentrated under reduced pressure. To the resulting residue, 500 ml of methanol and 20 ml of triethylamine were added and the mixture was stirred at room temperature for an hour. The solvent was distilled off under reduced pressure and the residue was extracted with 1 liter of ethyl acetate. The extract was washed in sequence with saturated aqueous sodium bicarbonate solution and then saturated sodium chloride aqueous solution. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The obtained crude product was recrystallized from isopropyl ether to give 19.0 g of white crystalline methyl 11-methoxy-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate.

Workup

  1. customobtained in Reference Example 2
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionTo the resulting residue, 500 ml of methanol and 20 ml of triethylamine were added
  4. stirringthe mixture was stirred at room temperature for an hour
  5. distillationThe solvent was distilled off under reduced pressure
  6. extractionthe residue was extracted with 1 liter of ethyl acetate
  7. washThe extract was washed in sequence with saturated aqueous sodium bicarbonate solution
  8. dry with materialAfter drying over anhydrous sodium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe obtained crude product
  11. customwas recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-7338df9db8b54011b5f05a916332c263
Source dataset
uspto-grants-1989_11
Patent number
US04882351

Reaction notes

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