m-Chloroperbenzoic acid → N-methyl-4-(2-(methylsulfinyl)benzo[d]oxazol-6-yloxy)picolinamide

HRID 2370491

Reaktionsgleichung

Reaktionsgleichung von HRID 2370491
[CH3:1][S:2][C:3]1[O:4][C:5]2[CH:11]=[C:10]([O:12][C:13]3[CH:18]=[CH:17][N:16]=[C:15]([C:19]([NH:21][CH3:22])=[O:20])[CH:14]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1.ClC1C=C(C=CC=1)C(OO)=[O:28]>C(Cl)Cl>[CH3:1][S:2]([C:3]1[O:4][C:5]2[CH:11]=[C:10]([O:12][C:13]3[CH:18]=[CH:17][N:16]=[C:15]([C:19]([NH:21][CH3:22])=[O:20])[CH:14]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1)=[O:28]

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 577256324-(2-(methylthio)benzo[d]oxazol-6-yloxy)-N-methylpyridine-2-carboxamide

Produkt 1

HCID 57725414N-methyl-4-(2-(methylsulfinyl)benzo[d]oxazol-6-yloxy)picolinamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of the 4-(2-(methylthio)benzo[d]oxazol-6-yloxy)-N-methylpyridine-2-carboxamide (1.26 g, 4.0 mmol, 1.0 eq) in 40 mL of methylene chloride was added 3-chloroperoxybenzoic acid (70%, 989 mg, 4.4 mmol, 1.1 eq). The reaction mixture was stirred at room temperature for 5 hours and then was diluted with 200 mL of methylene chloride. The resulting mixture was washed with aqueous sodium bicarbonate and brine then dried over MgSO4, filtered, and evaporated under reduced pressure to give crude product, which was used to next step without further purification. MH+=332.

Aufarbeitung

  1. washThe resulting mixture was washed with aqueous sodium bicarbonate and brine
  2. dry with materialthen dried over MgSO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customto give crude product, which
  6. customwas used to next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-2f95c9273f754826ab92d205e93c6594
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08710048B2

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