Ethanol → HCID 13134784, compound

HRID 444326Notes

Reaction equation

HRID 444326 reaction equation
O=[C:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[N:12][C:6]=2[S:5][C:4]2[CH:13]=[CH:14][C:15]([CH2:17][C:18]([OH:20])=[O:19])=[CH:16][C:3]1=2.O.NN.C(O)C.[OH-].[Na+]>C(O)(=O)C.C(O)COCCO>[N:12]1[C:6]2[S:5][C:4]3[CH:13]=[CH:14][C:15]([CH2:17][C:18]([OH:20])=[O:19])=[CH:16][C:3]=3[CH2:2][CH2:8][C:7]=2[CH:9]=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 12876536HCID 12876536, compound

Product 1

HCID 13134784HCID 13134784, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8117Diethylene GlycolSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 400 mg of (5,6-dihydro-6-oxo benzo[b]pyrido[3,2-f]thiepin-8-yl)-acetic acid, 800 mg of hydrazine hydrate and 30 ml of ethanol was refluxed for 3 hours. The solvent was distilled off to obtain a solid substance, to which were added 1 g of sodium hydroxide and 8 ml of diethylene glycol, and the mixture was stirred under a nitrogen atmosphere at 135° C. for 1.5 hours. After cooling, ice water was added to the mixture, and the resulting mixture was acidified with acetic acid and extracted with chloroform. The extract was washed with water and dried over anhydrous sodium sulfate. The solvent was removed by distillation to obtain an oil, which was chromatographed over silica gel and eluted with chloroform ethanol (100/1) to obtain a powder. This was recrystallized from 290 mg (yield: 76%) of (5,6-dihydro benzo[b]pyrido[3,2-f]thiepin-8-yl)-acetic acid as colorless needle crystals.

Workup

  1. temperaturewas refluxed for 3 hours
  2. distillationThe solvent was distilled off
  3. customto obtain a solid substance
  4. temperatureAfter cooling
  5. extractionextracted with chloroform
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was removed by distillation
  9. customto obtain an oil, which
  10. customwas chromatographed over silica gel
  11. washeluted with chloroform ethanol (100/1)
  12. customto obtain a powder

Sources & evidence

ORD record
ord-65668ba4568b4e4fa5f039446f529516
Source dataset
uspto-grants-1981_04
Patent number
US04263437

Reaction notes

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