Hydrochloric Acid → HCID 12895867, compound

HRID 893999Notes

Reaction equation

HRID 893999 reaction equation
[Cl:1][C:2]1[C:7]2[CH2:8][C:9](=[O:22])[C:10]3[CH:16]=[C:15]([CH:17]([CH3:21])[C:18](N)=[O:19])[CH:14]=[CH:13][C:11]=3[S:12][C:6]=2[CH:5]=[CH:4][CH:3]=1.[OH-:23].[Na+].Cl>O.O1CCCC1.CO>[Cl:1][C:2]1[C:7]2[CH2:8][C:9](=[O:22])[C:10]3[CH:16]=[C:15]([CH:17]([CH3:21])[C:18]([OH:23])=[O:19])[CH:14]=[CH:13][C:11]=3[S:12][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12895866HCID 12895866, compound

Product 1

HCID 12895867HCID 12895867, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 200 mg of 2-(9-chloro-10,11-dihydro-11-oxodibenzo[b,f]thiepin-2-yl)-propionamide, 3 g of sodium hydroxide, 25 ml of water, 30 ml of methanol and 2 ml of tetrahydrofuran was refluxed for 14 hours. After the completion of the reaction, the solvent was removed by distillation to obtain a residue, to which was added water, and the mixture was acidified with with 10% hydrochloric acid and then extracted with chloroform. The extract was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain crystals, which were chromatographed over silica gel and eluted with chloroform. The thus obtained product was recrystallized from ethyl acetate to give 95 mg (yield: 48%) of 2-(9-chloro-10,11-dihydro-11-oxodibenzo[b,f]thiepin-2-yl)-propionic acid as light yellow crystals having a melting point of 163°-164° C.

Workup

  1. temperaturewas refluxed for 14 hours
  2. customAfter the completion of the reaction
  3. customthe solvent was removed by distillation
  4. customto obtain a residue
  5. extractionextracted with chloroform
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off
  9. customto obtain crystals, which
  10. customwere chromatographed over silica gel
  11. washeluted with chloroform
  12. customThe thus obtained product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ca6f05cdaa414bdaab1b7f1c9b56977d
Source dataset
uspto-grants-1981_08
Patent number
US04282245

Reaction notes

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