Water → 2-Methoxymethyl-4-propyl-5-(4-aminobenzyl)thiazole

Reaction equation

[CH3:1][O:2][CH2:3][C:4]1[S:5][C:6]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)=[C:7]([CH2:9][CH2:10][CH3:11])[N:8]=1.O>CO.[Ni]>[CH3:1][O:2][CH2:3][C:4]1[S:5][C:6]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([NH2:19])=[CH:17][CH:18]=2)=[C:7]([CH2:9][CH2:10][CH3:11])[N:8]=1

Participants

Procedure

0.9 of 2-methoxymethyl-4-propyl-5-(4-nitrobenzyl)thiazole in 50 ml of methanol is hydrogenated at normal pressure and room temperature in the presence of Raney nickel. After filtration of the catalyst and concentration of the filtrate, the brown oil obtained is taken up with acidified water. The aqueous phase is extracted with ether, rendered basic with dilute sodium hydroxide and extracted with ethyl acetate. The organic phase is dried and concentrated to give 0.5 g of 2-methoxymethyl-4-propyl-5-(4-aminobenzyl)thiazole in the form of an orange oil, which is used as such for the next step.