Water → 5-Chloro-2-({[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfanyl)-1,3-oxazole

HRID 1511520Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1511520
[F:1][CH:2]([F:21])[O:3][C:4]1[N:8]([CH3:9])[N:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[C:5]=1[CH2:14][S:15][C:16]1[O:17][CH:18]=[CH:19][N:20]=1.[Cl:22]N1C(=O)CCC1=O.O>CN(C)C=O>[Cl:22][C:18]1[O:17][C:16]([S:15][CH2:14][C:5]2[C:6]([C:10]([F:12])([F:13])[F:11])=[N:7][N:8]([CH3:9])[C:4]=2[O:3][CH:2]([F:1])[F:21])=[N:20][CH:19]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 462224072-({[5-(Difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfanyl)-1,3-oxazole

Produkt 1

HCID 866510135-Chloro-2-({[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfanyl)-1,3-oxazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-({[5-(Difluoromethoxy)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfanyl)-1,3-oxazole (1.02 g, 3 mmol) is initially charged in 15 ml of dimethylformamide. N-Chlorosuccinimide (0.550 g, 4 mmol) is then added a little at a time with stirring. The mixture is stirred at 40° C. for a further 4 hours. For work-up, the reaction mixture is added to water and extracted twice with dichloromethane, and the extracts are then washed with water and finally with saturated NaCl solution. The combined organic phases are dried over magnesium sulfate, filtered off and concentrated. The crude product is purified chromatographically (heptane:ethyl acetate, gradient 10:0 to 7:3). This gives 0.45 g of product (35.9% of theory).

Aufarbeitung

  1. stirringThe mixture is stirred at 40° C. for a further 4 hours
  2. extractionextracted twice with dichloromethane
  3. washthe extracts are then washed with water and finally with saturated NaCl solution
  4. dry with materialThe combined organic phases are dried over magnesium sulfate
  5. filtrationfiltered off
  6. concentrationconcentrated
  7. customThe crude product is purified chromatographically (heptane:ethyl acetate, gradient 10:0 to 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-410092df733d49249777d9a652e4a99e
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08216973B2

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