Ammonia → N2-methyl-5-trifluoromethylsulfanylpyridine-2,3-diamine

HRID 1750053Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1750053
Br[C:2]1[C:3]([NH:13][CH3:14])=[N:4][CH:5]=[C:6]([S:8][C:9]([F:12])([F:11])[F:10])[CH:7]=1.C(CC(=O)C)(=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].[NH3:28]>[Cu+2].C(CC(=O)C)(=O)C.O.CN1C(=O)CCC1>[CH3:14][NH:13][C:3]1[C:2]([NH2:28])=[CH:7][C:6]([S:8][C:9]([F:12])([F:11])[F:10])=[CH:5][N:4]=1

Komponenten

8

Edukt 4

HCID 222AmmoniaHCID 10796Cesium carbonateHCID 31261AcetylacetoneHCID 67981267(3-Bromo-5-trifluoromethylsulfanylpyridine-2-yl)-methylamine

Produkt 1

HCID 68091243N2-methyl-5-trifluoromethylsulfanylpyridine-2,3-diamine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 21863952acetylacetone copper(II)KatalysatorHCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

1.96 g of (3-bromo-5-trifluoromethylsulfanylpyridin-2-yl)-methylamine, 89 mg of acetylacetone copper(II), 0.27 g of acetylacetone, 2.34 g of cesium carbonate, 7 ml of NMP and 5 ml of aqueous ammonia (28%) were charged to a pressure-resistant reactor and stirred at 110° C. for 8.5 hours. Water was added to the reaction mixture cooled to room temperature, and the insoluble matter was filtered with celite (registered trademark), and then the filtered matter was washed with ethyl acetate, and the filtrate was extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 1.18 g of N2-methyl-5-trifluoromethylsulfanylpyridine-2,3-diamine.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. filtrationthe insoluble matter was filtered with celite (registered trademark)
  3. washthe filtered matter was washed with ethyl acetate
  4. extractionthe filtrate was extracted with ethyl acetate
  5. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0348384267e94c4f870e3c1b538a9756
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156838B2

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