Chloroform → HCID 23337057, compound

HRID 903650Notes

Reaction equation

HRID 903650 reaction equation
[Cl:1][C:2]1[C:7]2[CH2:8][CH:9](O)[C:10]3[CH:16]=[C:15]([O:17][CH2:18][CH3:19])[CH:14]=[CH:13][C:11]=3[S:12][C:6]=2[CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.C(Cl)(Cl)Cl>O>[Cl:1][C:2]1[C:7]2[CH2:8][CH2:9][C:10]3[CH:16]=[C:15]([O:17][CH2:18][CH3:19])[CH:14]=[CH:13][C:11]=3[S:12][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 24386Thionyl ChlorideHCID 23337062HCID 23337062, compound

Product 1

HCID 23337057HCID 23337057, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of 1.1 g of 9-chloro-10,11-dihydro-2-ethoxy-11-hydroxydibenzo[b,f]thiepin and 33 ml of thionyl chloride was refluxed for 3 hrs. and evaporated to obtain the residue, to which was added 50 g of ice-water. The resulting mixture was extracted with chloroform and the extract was washed with water and dried over calcium chloride. The solvent was evaporated to obtain the concentrated which was added with stirring at room temperature to a mixutre of 70 ml of anhydrous tetrahydrofuran and 400 mg of lithium aluminum hydride. The thus obtained mixture was refluxed with stirring for 4 hrs., to which was added 30% sodium hydroxide solution with stirring under cooling with a mixture of ice and sodium chloride. The mixture was filtered and the filtrate was evaporated to obtain the residue, to which was added 100 ml of chloroform and 100 ml of water, and the chloroform layer was collected. This was washed with water, dried and the solvent was evaporated to obtain 520 mg of 9-chloro-10,11-dihydro-2-ethoxydibenzo[b,f]thiepin as oily substance.

Workup

  1. temperaturewas refluxed for 3 hrs
  2. customand evaporated
  3. customto obtain the residue
  4. extractionThe resulting mixture was extracted with chloroform
  5. washthe extract was washed with water
  6. dry with materialdried over calcium chloride
  7. customThe solvent was evaporated
  8. customto obtain the
  9. concentrationconcentrated which
  10. additionwas added
  11. temperatureThe thus obtained mixture was refluxed
  12. stirringwith stirring for 4 hrs
  13. addition, to which was added 30% sodium hydroxide solution
  14. stirringwith stirring
  15. temperatureunder cooling with a mixture of ice and sodium chloride
  16. filtrationThe mixture was filtered
  17. customthe filtrate was evaporated
  18. customto obtain the residue
  19. customthe chloroform layer was collected
  20. washThis was washed with water
  21. customdried
  22. customthe solvent was evaporated

Sources & evidence

ORD record
ord-6ad1ce3a98094bc99d0313662ee82dfb
Source dataset
uspto-grants-1980_10
Patent number
US04228284

Reaction notes

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