Hydrochloric Acid → HCID 15886891, compound

HRID 651576Notes

Reaction equation

HRID 651576 reaction equation
[OH-].[K+].[CH:3]1[C:8]2[C:9]3[NH:10][C:11]4[C:16]([C:17]=3[CH:18]([C:20]([O:22]CC)=[O:21])[S:19][C:7]=2[CH:6]=[CH:5][CH:4]=1)=[CH:15][CH:14]=[CH:13][CH:12]=4.Cl>O.C(O)C>[CH:3]1[C:8]2[C:9]3[NH:10][C:11]4[C:16]([C:17]=3[CH:18]([C:20]([OH:22])=[O:21])[S:19][C:7]=2[CH:6]=[CH:5][CH:4]=1)=[CH:15][CH:14]=[CH:13][CH:12]=4

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 21709030HCID 21709030, compound

Product 1

HCID 15886891HCID 15886891, compoundYield 101.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 19.46 g of potassium hydroxide in 40 ml of water was added to a solution of 21.63 g of ethyl 6,11-dihydro-5-thia-11-aza-benzo[a]fluoren-6-carboxylate in 100 ml of ethanol. After reflux under heating for 2 hours, the reaction solution was adjusted to pH 3 with conc. hydrochloric acid, and extracted with ethyl acetate. 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 19.94 g of 6,11-dihydro-5-thia-11-aza-benzo[a]fluoren-6-carboxylic acid.

Workup

  1. temperatureAfter reflux
  2. temperatureunder heating for 2 hours
  3. extractionextracted with ethyl acetate
  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-fad3f20af3f5483f84f33d5f13404584
Source dataset
uspto-grants-2001_08
Patent number
US06281355B1

Reaction notes

Loading…