1H-1,2,4-Triazole → HCID 19811645, compound
Reaction equation
Br[CH2:2][C:3]1[CH:15]=[C:14]2[C:6]([CH:7]=[CH:8][C:9]3[O:10][C:11](=[O:18])[C:12]([CH3:17])([CH3:16])[C:13]=32)=[CH:5][CH:4]=1.[NH:19]1[CH:23]=[N:22][CH:21]=[N:20]1>C(#N)C>[CH3:16][C:12]1([CH3:17])[C:11](=[O:18])[O:10][C:9]2[CH:8]=[CH:7][C:6]3[C:14]([C:13]1=2)=[CH:15][C:3]([CH2:2][N:19]1[CH:23]=[N:22][CH:21]=[N:20]1)=[CH:4][CH:5]=3Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 8-bromomethyl-1,1-dimethyl-2(1H)-naphtho[2,1-b]furanone in acetonitrile (5 ml), was treated with 1,2,4-triazole (1.4 g) and the mixture was heated under reflux for 18 h. The solution was evaporated to dryness under reduced pressure and the residue was partitioned between 1N aqueous sodium hydrogen carbonate and ethyl acetate. The ethyl acetate extract was separated, dried and evaporated to dryness, and the residue was purified by flash chromatography. Elution with methanol:chloroform, 1:49 v/v, gave 1,1-dimethyl-8-(1H-1,2,4-triazol-1-ylmethyl)-2-(1H)-naphtho[2,1-b]furanone, m.p. 136°-137° after recrystallisation from a mixture of ethyl acetate and cyclohexane.