Thiazole → HCID 10774002, compound

Participants

Reaction Conditions

Reaction Steps

In a bomb tube, a mixture of 3.7 g (20 mmol) of 4-bromobenzaldehyde (Fluka, Buchs, Switzerland), 6.64 ml (93 mmol) of thiazole, 2.94 g of potassium acetate and 1.16 g (1 mmol) of Pd(PPh3)4 in 50 ml of dimethylacetamide is stirred at 150° C. for 12 hours. The reaction mixture is concentrated by evaporation. Water is added to the residue and the mixture is extracted 3× with methylene chloride. The organic phases are filtered through cotton wadding, concentrated by evaporation and chromatographed (SiO2; hexane/ethyl acetate 1:2), yielding the title compound: HPLC20-100: tRet=11.4; 1H-NMR (CD3OD) δ 9.98 (s, HCO), 9.03 (s, H(2)thiazole), 8.32 (s, H(4)thiazole), 7.95 and 7.85 (2d, J=8, each 2H); additionally also signals of the hydrate (≈12%): 8.92 (s, H(2)thiazole), 8.15 (s, H(4)thiazole), 7.62 and 7.53 (2d, J=8, each 2H), 5.54 (s, HC(OH)2).

Provenance & Evidence