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.[CH3:23][CH2:24]O>OS(O)(=O)=O>[CH2:23]([O:14][C:12]([CH:4]1[C:3]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:21][C:2]=2[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[S:5]1)=[O:13])[CH3:24]

Participants

Procedure

To a solution of 4-oxo-thiochroman-2-carboxylic acid (3 g, 14 mmol) and phenyl hydrazine (1.4 ml, 14 mmol) in EtOH (14 ml), H2SO4 (1.8 ml) was added, and the mixture was heated at reflux for 5 hr. The reaction was cooled to room temperature and the solid, which formed overnight, was filtered, washed with cold EtOH and cold Et2O to give 2.26 g (51%) of 6,11-dihydro-5-thia-11-aza-benzo[α]fluorene-6-carboxylic acid ethyl ester as a crème solid. 1H NMR (CDCl3) δ 8.47 (1H, br s), 7.53-7.58 (1H, m), 7.10-7.40 (7H, m), 5.00 (1H, s), 4.09 (2H, q), 1.15 (3H, t).