HCID 21834217, compound → HCID 57203651, compound

Reaction equation

N[C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH2:8][CH:7]([C:10]([N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])=[O:11])[C:6]=2[CH:19]=1.N([O-])=[O:21].[Na+]>S(=O)(=O)(O)O.O>[OH:21][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH2:8][CH:7]([C:10]([N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])=[O:11])[C:6]=2[CH:19]=1

Participants

Procedure

11.6 g of 5-amino-2,3-dihydro-N,N-dipropyl-3-benzothiophencarboxamide were dissolved in a mixture of 4 ml of conc. sulphuric acid and 40 ml of water. 3.1 g of sodium nitrite dissolved in 10 ml of water were added dropwise below 10° C. with stirring. After addition the mixture was stirred for further 0.5 hours. The diazonium solution was then added carefully to a pre-heated solution of 50 ml of conc. sulphuric acid in 40 ml of water at 115°-120° C. The resulting mixture was poured onto ice and subsequently extracted with dichloromethane. Yield of the title compound as a semicrystalline product: 8.7 g.