2-bromo-6,7-dimethoxy-3,4-dihydronaphthalen-1(2H)-one → 1-(7,8-Dimethoxy-4,5-dihydronaphtho[1,2-d]thiazol-2-yl)hydrazine
Reaction equation
Br[CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([O:14][CH3:15])=[C:7]([O:12][CH3:13])[CH:8]=2)[C:3]1=O.[NH2:17][NH:18][C:19]([NH2:21])=[S:20]>O1CCOCC1>[CH3:13][O:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][C:6]=1[O:14][CH3:15])[C:3]1[N:21]=[C:19]([NH:18][NH2:17])[S:20][C:2]=1[CH2:11][CH2:10]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 400 mg (1.4 mmol) of 2-bromo-6,7-dimethoxy-3,4-dihydronaphthalen-1(2H)-one and thiosemicarbazide (127 mg, 1.4 mmol) in 20 ml of anhydrous dioxane was stirred at 80° C. for 24 h. The resulting yellow precipitate was filtered and washed with dioxane (10 ml). The dried precipitate was then basified with 2 M Sodium Carbonate (20 ml) solution. The formed pale brown product was filtered at the pump and washed with water. The LCMS analysis showed the formation of the required 1-(7,8-dimethoxy-4,5-dihydronaphtho[1,2-d]thiazol-2-yl)hydrazine along with 7,8-dimethoxy-4,5-dihydro-4aH-naphtho[1,2-e][1,3,4]thiadiazin-3-amine.