Ethanol → HCID 13134786, compound

HRID 355112Notes

Reaction equation

HRID 355112 reaction equation
[N:1]1[C:11]2[S:10][C:9]3[CH:12]=[CH:13][C:14]([CH2:16][C:17]([OH:19])=[O:18])=[CH:15][C:8]=3[CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.C(=O)([O-])O.[Na+].[CH2:30](O)[CH3:31]>>[N:1]1[C:11]2[S:10][C:9]3[CH:12]=[CH:13][C:14]([CH2:16][C:17]([O:19][CH2:30][CH3:31])=[O:18])=[CH:15][C:8]=3[CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 13134784HCID 13134784, compound

Product 1

HCID 13134786HCID 13134786, compoundYield 85%

Procedure

A mixture of 30 mg of (5,6-dihydro benzo[b]pyrido[3,2-f]-thiepin-8-yl)-acetic acid, 3 ml of ethanol and 100 mg of sulfuric acid was refluxed for 1 hour. After the completion of the reaction, the solvent was distilled off to obtain a residue, to which was added ice water, and the mixture was basified with a 5% sodium hydrogen carbonate solution and extracted with ethyl acetate. 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 benzene/chloroform (2/1), thereby yielding 28 mg (yield: 85%) of ethyl (5,6-dihydro benzo[b]pyrido[3,2-f]thiepin-8-yl)-acetate as an oil.

Workup

  1. temperaturewas refluxed for 1 hour
  2. customAfter the completion of the reaction
  3. distillationthe solvent was distilled off
  4. customto obtain a residue
  5. extractionextracted with ethyl acetate
  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 benzene/chloroform (2/1)

Sources & evidence

ORD record
ord-4f1b0a46542a4cf190d70ac01d57ba6e
Source dataset
uspto-grants-1983_03
Patent number
US04377702

Reaction notes

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