Ethanol → HCID 21709030, compound

HRID 651575Notes

Reaction equation

HRID 651575 reaction equation
O=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[S:5][CH:4]([C:12]([OH:14])=[O:13])[CH2:3]1.[C:15]1([NH:21]N)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.S(=O)(=O)(O)O.[CH2:28](O)[CH3:29]>>[CH:10]1[C:11]2[C:2]3[NH:21][C:15]4[C:20]([C:3]=3[CH:4]([C:12]([O:14][CH2:28][CH3:29])=[O:13])[S:5][C:6]=2[CH:7]=[CH:8][CH:9]=1)=[CH:19][CH:18]=[CH:17][CH:16]=4

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 7516PhenylhydrazineHCID 11839188HCID 11839188, compound

Product 1

HCID 21709030HCID 21709030, compound

Procedure

To a solution of 22.54 g of (4-oxo-thiochroman-2-yl)carboxylic acid and 10.7 ml of phenylhydrazine in 100 ml of ethanol was added 15 ml of sulfuric acid, followed by reflux under heating for 5 hours. The reaction solution was cooled to room temperature, poured into 500 ml of ice water and extracted with ether. The extract was washed with a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure, and the residue was recrystallized from ethanol-hexane to give 21.85 g of ethyl 6,11-dihydro-5-thia-11-aza-benzo[a]fluoren-6-carboxylate.

Workup

  1. temperatureby reflux
  2. temperatureunder heating for 5 hours
  3. extractionextracted with ether
  4. washThe extract was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter removal of the drying agent
  7. filtrationby filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customthe residue was recrystallized from ethanol-hexane

Sources & evidence

ORD record
ord-cf505bc4bbee4060bf3402fff5e23143
Source dataset
uspto-grants-2001_08
Patent number
US06281355B1

Reaction notes

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