Furfural → HCID 178478186、化合物

反応式

[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:14]=[C:13]([NH2:15])[NH:12][N:11]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH:16](=O)[C:17]1[O:21][CH:20]=[CH:19][CH:18]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:14]=[C:13]([NH:15][CH2:16][C:17]3[O:21][CH:20]=[CH:19][CH:18]=3)[NH:12][N:11]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

参加物

実験手順

A solution of N3-(3,5-dichlorophenyl)-1H-1,2,4-triazole-3,5-diamine Intermediate 2 (70 mg, 287 μmol) and furfural (85.1 mg, 886 μmol) in MeOH (3 ml) was stirred at room temperature for 3 days. The resulting suspension was filtered to collect the solid. The solid was re-suspended in MeOH (5 ml), NaBH4 (65.1 mg, 1.72 mmol) was added and the reaction was stirred for 1 hour. The solvent was removed, and the reaction mixture was redissolved in DCM and washed with water (2×4 ml), dried over MgSO4 and concentrated to give a solid. Trituration with DCM/Hexanes afforded a white solid as desired product (50.5 mg, 54% yield). MS +m/z: 324 (M+H)+