تفاعل #1583814

ord-0c546883ac6a4eeb9386a2bcfbc1e624

معادلة التفاعل

OO
hydrogen peroxide
CCc1nc(-c2ccc(F)cc2)c(-c2ccncc2)s1
4-[2-ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]pyridine
CCc1nc(-c2ccc(F)cc2)c(-c2cc[n+]([O-])cc2)s1
desired product
المردود 85.0%
CCc1nc(-c2ccc(F)cc2)c(-c2cc[n+]([O-])cc2)s1
4-[2-Ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]pyridine 1-oxide
المردود 85.0%

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىdoes not exceed 15° C.
  2. 2
    غسيلthe organic phase is washed successively with 30 ml of a saturated aqueous NaHCO3 solution, 30 ml of a saturated Na2SO3 solution and 30 ml of water
  3. 3
    تجفيفdried over MgSO4

الإجراء التجريبي

3.9 ml (44 mmol) of a 30% strength hydrogen peroxide solution are added dropwise with cooling to a solution of 2.18 g (7.24 mmol) of 4-[2-ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]pyridine and 46.2 mg (0.19 mmol) of methyltrioxorhenium (VII) in 10 ml dichloromethane such that the temperature of the reaction mixture does not exceed 15° C., and the mixture is stirred at room temperature for 16 h. The reaction mixture is then diluted with 100 ml of dichloromethane, and the organic phase is washed successively with 30 ml of a saturated aqueous NaHCO3 solution, 30 ml of a saturated Na2SO3 solution and 30 ml of water and dried over MgSO4. Under reduced pressure, the product is freed from the solvent, giving 1.98 g (85%) of the desired product; 1H-NMR(DMSO-d6) δ: 8.12 (d, 2H), 7.53 (m, 2H), 7.25 (d, 2H), 7.21 (m, 2H), 3.03 (q, 2H), 1.36 (t, 3H).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09198426B2uspto-grants-2015_12