Hydrochloric Acid → HCID 53728888、化合物

反応式

[CH3:1][NH:2][C:3]1[S:4][C:5]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[C:6]([CH:8]=O)[N:7]=1.[OH2:16].Cl.[O:18]1[CH2:22]C[CH2:20][CH2:19]1>>[CH3:1][NH:2][C:3]1[S:4][C:5]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[C:6]([CH:8]=[CH:20][C:19]([O:18][CH3:22])=[O:16])[N:7]=1

参加物

反応物 4

HCID 313Hydrochloric Acid

HCID 962Water

HCID 8028Tetrahydrofuran

HCID 20144978HCID 20144978、化合物

生成物 1

HCID 53728888HCID 53728888、化合物

実験手順

A mixture of 2-methylamino-4-formyl-5-(4-pyridyl)thiazole (1.1 g) and triphenylphosphinecarbomethoxymethylene (3.34 g) in tetrahydrofuran (80 ml) was stirred at 40° to 45° C. for 2.5 hours. The reaction mixture was poured into water and the resultant solution was acidified to pH 1.0 with 10% hydrochloric acid. The acidified solution was washed with ethyl acetate. The aqueous solution was adjusted to pH 7.0 with 20% aqueous potassium carbonate and extracted with ethyl acetate. The organic extract was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was subjected to column chromatography on silica gel eluting with a mixture of ethyl acetate and tetrahydrofuran (8:2). The fractions containing the desired compound were combined and evaporated in vacuo to give methyl 2-methylamino-5-(4-pyridyl)-4-thiazoleacrylate (trans isomer) (0.66 g). mp 166°-167° C.