Acetic Acid → HCID 12895879, compound

HRID 894007Notes

Reaction equation

HRID 894007 reaction equation
Cl.[N+:2]([C:5]1[CH:6]=[CH:7][C:8]2[S:14][C:13]3[CH:15]=[CH:16][C:17]([CH:19]([CH3:23])[C:20](N)=[O:21])=[CH:18][C:12]=3[C:11](=[O:24])[CH2:10][C:9]=2[CH:25]=1)([O-:4])=[O:3].C(O)(=[O:28])C>>[N+:2]([C:5]1[CH:6]=[CH:7][C:8]2[S:14][C:13]3[CH:15]=[CH:16][C:17]([CH:19]([CH3:23])[C:20]([OH:28])=[O:21])=[CH:18][C:12]=3[C:11](=[O:24])[CH2:10][C:9]=2[CH:25]=1)([O-:4])=[O:3]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 12895878HCID 12895878, compound

Product 1

HCID 12895879HCID 12895879, compoundYield 43%

Procedure

A mixture of 3 ml of conc. hydrochloric acid, 3 ml of acetic acid and 0.33 g of 2-(10,11-dihydro-8-nitro-11-oxodibenzo[b,f]thiepin-2-yl)-propionamide was refluxed with stirring for 3.5 hours. The reaction mixture was concentrated, and to this was added water. Threafter, the resulting mixture was extracted with ethyl acetate, and the extract was reextracted with a saturated sodium hydrogen carbonate solution. The extract was acidified with hydrochloric acid and extracted with ethyl acetate. The extract was washed with a saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain a brown solid substance, which was chromatographed over 6 g of silica gel and eluted with chloroform, and there were obtained light yellow crystals. The thus obtained crystals were recrystallized from chloroform to give 0.14 g (yield: 43%) of 2-(10,11-dihydro-8-nitro-11-oxodibenzo[b,f]thiepin-2-yl)-propionic acid as a light yellow powder having a melting point of 209.5°-211° C.

Workup

  1. temperaturewas refluxed
  2. concentrationThe reaction mixture was concentrated
  3. additionto this was added water
  4. extractionThreafter, the resulting mixture was extracted with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with a saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off
  9. customto obtain a brown solid substance, which
  10. customwas chromatographed over 6 g of silica gel
  11. washeluted with chloroform
  12. customthere were obtained light yellow crystals
  13. customThe thus obtained crystals were recrystallized from chloroform

Sources & evidence

ORD record
ord-db7a50020a304b1693c28778ecaaa803
Source dataset
uspto-grants-1981_08
Patent number
US04282245

Reaction notes

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