Hydrochloric Acid → HCID 20144978, compound

Reaction equation

[CH3:1][NH:2][C:3]1[S:4][C:5]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[C:6]([C:8](OCC)=[O:9])[N:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1>[CH:8]([C:6]1[N:7]=[C:3]([NH:2][CH3:1])[S:4][C:5]=1[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)=[O:9]

Participants

Procedure

To a solution of ethyl 2-methylamino-5-(4-pyridyl)-4-thiazolecarboxylate (2.6 g) in dry tetrahydrofuran (120 ml) was added lithium aluminum hydride (0.38 g) at -10° C. with stirring, which was continued at -10°~-3° C. for 30 minutes. The reaction mixture was poured into ice-water and the resultant solution was acidified to pH 1.0 with 10% hydrochloric acid. The insoluble material was filtered off. The filtrate was adjusted to pH 7.0 with 20% aqueous solution of potassium carbonate and extracted with a mixture of ethyl acetate and tetrahydrofuran. The organic extract was concentrated in vacuo. The precipitate was collected by filtration, washed with ethyl acetate and dried in vacuo to give 4-formyl-2-methylamino-5-(4-pyridyl)thiazole (0.8 g). mp 243°-245° C. (dec.).