Reaktion #1366574

Reaktionsgleichung

Ethyl acetate

N-(3,5-Dichloropyridin-4-yl)-4-difluoromethoxy-3-cyclopropylmethoxybenzamide

magnesium monoperoxyphthalate hexahydrate

magnesium monoperoxyphthalate hexahydrate

→

N-(3.5-Dichloro-1-oxido-pyridin-4-yl)-4-difluoromethoxy-3-cyclopropylmethoxybenzamide

Ausbeute 63.8%

Lösungsmittel

CH2Cl2 MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder reflux for 48 h
2. 2
   workup.STIRRINGthe reaction mixture was stirred
3. 3
   Temperaturunder reflux for an additional 24 h
4. 4
   Waschenthe organic phase was washed by 25% aqueous NH4OAc, water and brine
5. 5
   Trocknendried (MgSO4)
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe residue was purified by column chromatography on silica (EtOAc)

Vorschrift

A mixture of N-(3,5-Dichloropyridin-4-yl)-4-difluoromethoxy-3-cyclopropylmethoxybenzamide (3.0 g, 7.4 mmol) and magnesium monoperoxyphthalate hexahydrate (“MMPP”) (7.36 g, 14.9 mmol) in CH2Cl2/MeOH (10 mL) was stirred under reflux for 48 h. An additional amount of magnesium monoperoxyphthalate hexahydrate (7.4 g, 15 mmol) was added and the reaction mixture was stirred under reflux for an additional 24 h. Ethyl acetate was then added and the organic phase was washed by 25% aqueous NH4OAc, water and brine, dried (MgSO4) and concentrated. The residue was purified by column chromatography on silica (EtOAc) to yield N-(3.5-Dichloro-1-oxido-pyridin-4-yl)-4-difluoromethoxy-3-cyclopropylmethoxybenzamide (Compound I) as a white solid (1.98 g, 63%). 1H NMR (500 MHz, acetone-d6): δ 0.40 (m, 2H), 0.60 (m, 2H), 1.30 (m, 1H), 4.0 (d, 2H), 7.05 (t, 1H), 7.35 (d, 1H), 7.7 (m, 1H), 7.75 (s, 1H), 8.40 (s, 2H), 9.6 (bs, 1H).

Quelle