Hydrochloric Acid → HCID 12895865, compound

HRID 893998Notes

Reaction equation

HRID 893998 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[CH2:6][C:7](=[O:20])[C:8]3[CH:14]=[C:13]([CH:15]([CH3:19])[C:16](N)=[O:17])[CH:12]=[CH:11][C:9]=3[S:10][C:4]=2[CH:3]=1.[OH-:23].[K+].O.Cl>CCCCCC.CO.O1CCCC1>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[CH2:6][C:7](=[O:20])[C:8]3[CH:14]=[C:13]([CH:15]([CH3:19])[C:16]([OH:23])=[O:17])[CH:12]=[CH:11][C:9]=3[S:10][C:4]=2[CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 12895864HCID 12895864, compound

Product 1

HCID 12895865HCID 12895865, compoundYield 45.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A mixture of 0.2 g of 2-(7-chloro-10,11-dihydro-11-oxodibenzo[b,f]thiepin-2-yl)-propionamide, 10 g of potassium hydroxide, 60 ml of water, 20 ml of tetrahydrofuran and 200 ml of methanol was refluxed for 5 hours. The solvent was removed by distillation to obtain a residue, to which was added ice water, and the mixture was acidified with hydrochloric acid and extracted with chloroform. The extract was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain a residue, which was chromatographed over silica gel and eluted with chloroform/benzene (3/1), thereby obtaining a solid substance. This was recrystallized from benzene--n-hexane to give 91 mg (yield: 45%) of 2-(7-chloro-10,11-dihydro-11-oxodibenzo[b,f]thiepin-2-yl)-propionic acid as light yellow granular crystals having a melting point of 142°-143° C.

Workup

  1. temperaturewas refluxed for 5 hours
  2. customThe solvent was removed by distillation
  3. customto obtain a residue
  4. extractionextracted with chloroform
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off
  8. customto obtain a residue, which
  9. customwas chromatographed over silica gel
  10. washeluted with chloroform/benzene (3/1)
  11. customobtaining a solid substance
  12. customThis was recrystallized from benzene

Sources & evidence

ORD record
ord-64a90e83d77246f4b16aa8d51787bb78
Source dataset
uspto-grants-1981_08
Patent number
US04282245

Reaction notes

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