Ethanol → HCID 21709030, compound

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

Reactant 4

HCID 702Ethanol

HCID 1118Sulfuric Acid

HCID 7516Phenylhydrazine

HCID 118391884-Oxothiochromane-2-carboxylic acid

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.