Acetic Anhydride → 4-Acetamidothiazole
Reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.Cl.[S:9]1[CH:13]=[C:12]([NH2:14])[N:11]=[CH:10]1.C(N(CC)CC)C>C(Cl)Cl.O>[S:9]1[CH:13]=[C:12]([NH:14][C:5](=[O:7])[CH3:6])[N:11]=[CH:10]1Participants
6
C(O[C:5](=[O:7])[CH3:6])(=O)C.Cl.[S:9]1[CH:13]=[C:12]([NH2:14])[N:11]=[CH:10]1.C(N(CC)CC)C>C(Cl)Cl.O>[S:9]1[CH:13]=[C:12]([NH:14][C:5](=[O:7])[CH3:6])[N:11]=[CH:10]1Acetic anhydride (153 mg, 1.50 mmol) was added to the solution of thiazol-4-amine hydrochloride from example 2.2 (100 mg, 1.0 mmol) and triethylamine (152 mg, 1.50 mmol) in DCM (5 mL). The solution was stirred for overnight at room temperature. The reaction mixture was diluted with water, washed with 0.1 M HCl (10 mL), NaHCO3 solution and brine. The combined organic layers were dried with Na2SO4, filtered and concentrated. The resulting mixture was deposited onto silica gel and loaded onto a silica gel column and eluted with EA/PE (1:2) to aim product (55 mg, 0.39 mmol, 38.7%).
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