Acetic Acid → HCID 20338069, compound

HRID 1395761Notes

Reaction equation

HRID 1395761 reaction equation
[O:1]=[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]([CH:17]([CH3:21])[C:18]([OH:20])=[O:19])=[CH:16][C:3]1=2.[N+](=[CH2:24])=[N-].C(O)(=O)C.C(=O)([O-])O.[Na+]>C(O)C>[O:1]=[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]([CH:17]([CH3:21])[C:18]([O:20][CH3:24])=[O:19])=[CH:16][C:3]1=2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 9550DiazomethaneHCID 516892Sodium BicarbonateHCID 20506969HCID 20506969, compound

Product 1

HCID 20338069HCID 20338069, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 54 mg of 2-(5,6-dihydro-6-oxo benzo[b]pyrido[3,2-f]-thiepin-8-yl)-propionic acid in ethanol was added 5 ml of diazomethane etherial solution and the mixture was stirred at room temperature for 1 hour. To this was added acetic acid to decompose an excess reagent, then saturated sodium hydrogen-carbonate solution to make the solution alkaline, and the mixture was extracted with ethyl acetate. The extract was washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain 51 mg of oily substance, which was chromatographed over silica gel, eluted with benzene/chloroform (1/1) to obtain the colorless oily substance, which was crystallized from ethanol to give 40 mg of methyl 2-(5,6-dihydro-6-oxo benzo[b]pyrido[3,2-f]thiepin-8-yl)-propionate as colorless crystals having a melting point of 98°-99.5° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. customto obtain 51 mg of oily substance, which
  6. customwas chromatographed over silica gel
  7. washeluted with benzene/chloroform (1/1)
  8. customto obtain the colorless oily substance, which
  9. customwas crystallized from ethanol

Sources & evidence

ORD record
ord-ec3b34796d6d4a4798abcbcb6f80dc9f
Source dataset
uspto-grants-1980_05
Patent number
US04205170

Reaction notes

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