Guanidine Hydrochloride → HCID 178524219、化合物

反応式

C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[CH:11]=[CH:12]N(C)C)=[CH:6][CH:5]=1.Cl.[NH2:19][C:20]([NH2:22])=N.[OH-:23].[Na+]>CO>[OH:23][C:20]1[N:22]=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:17])=[O:2])=[CH:5][CH:6]=2)[CH:11]=[CH:12][N:19]=1

参加物

反応条件

温度: 80 °C

実験手順

To a suspension of 4-(3-Dimethylamino-acryloyl)-benzoic acid methyl ester (1 g, 4.29 mmol; Prepared according to the method reported by S. Murahashi et al. Bulletin of the Chemical Society of Japan, 1987, 60, 3285) in MeOH (8.5 mL) is added guanidine hydrochloride (1.23 g, 12.86 mmol) and NaOH (412 mg, 10.3 mmol). The mixture is stirred at 80° C. for 24 h and then cooled down to room temperature. The mixture is concentrated and treated with H2SO4/H2O (1:1, 20 mL) and heated to 120° C. for 14 h. After cooling down to room temperature, the mixture is basified by pouring into ice cold NH4OH (50 mL) and acidified to pH= 1 by adding concentrated hydrogen chloride solution. The precipitate is collected by filtration, washed with acetonitrile and dried in a vacuum oven for 24 h to yield 680 mg of crude 4-(2-hydroxy-pyrimidin-4-yl)-benzoic acid.