تفاعل #1905723

معادلة التفاعل

1-(4-{4-[[3-(2-chloro-acetyl)-phenyl]-(tetrahydro-pyran-2-yloxy)-methyl]-benzyloxy}-2-hydroxy-3-methyl-phenyl)-propan-1-one

thiourea

p-toluenesulfonic acid

→

title compound

المردود 52.1%

1-[4-(4-{[3-(2-amino-thiazol-4-yl)-phenyl]-hydroxy-methyl}-benzyloxy)-2-hydroxy-3-methyl-phenyl]-propan-1-one

المردود 52.1%

المذيبات

ethanol

ظروف التفاعل

المعالجة

1. 1
   أخرىMajor fraction isolated

الإجراء التجريبي

Heat a solution of 1-(4-{4-[[3-(2-chloro-acetyl)-phenyl]-(tetrahydro-pyran-2-yloxy)-methyl]-benzyloxy}-2-hydroxy-3-methyl-phenyl)-propan-1-one (0.250 mg, 0.466 mmol) and thiourea (71 mg, 0.931 mmol) in ethanol (0.20 M) overnight at 70° C. Add p-toluenesulfonic acid (10 mg) and stir overnight. Evaporate solvents and chromatograph residue. Major fraction isolated was the title compound (0.115 g, 0.243 mmol, 52%): 1H NMR (400 MHz, DMSO-d6) δ 1.09 (t, J=10.5 Hz, 3H), 2.02 (s, 3H), 3.03 (q, J=14.4 Hz, 2H), 5.20 (s, 2H), 5.75 (s, 1H), 6.70 (d, J=9.0 Hz, 1H), 7.14 (s, 1H), 7.37 (d, J=6.43 Hz, 1H), 7.42 (m, 6H), 7.60 (m, 1H), 7.80 (m, 2H), 12.89 (s, 1H). MS (m/z): 473 (M−H).

المصدر