Ethyl Acetate → HCID 24802657, Verbindung

HRID 1692715Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1692715
[N+:1]([C:4]1[CH:8]=[N:7][NH:6][C:5]=1[NH2:9])([O-:3])=[O:2].CN(C)[CH:12]=[CH:13][C:14]([C:16]1[CH:17]=[CH:18][C:19]([Cl:28])=[C:20]([N:22]([CH3:27])[S:23]([CH3:26])(=[O:25])=[O:24])[CH:21]=1)=O.C(OCC)(=O)C>C(O)(=O)C>[Cl:28][C:19]1[CH:18]=[CH:17][C:16]([C:14]2[N:6]3[N:7]=[CH:8][C:4]([N+:1]([O-:3])=[O:2])=[C:5]3[N:9]=[CH:12][CH:13]=2)=[CH:21][C:20]=1[N:22]([CH3:27])[S:23]([CH3:26])(=[O:25])=[O:24]

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 36139914-nitro-1H-pyrazol-5-amineHCID 67279091N-[2-chloro-5-(3-dimethylamino-acryloyl)-phenyl]-N-methyl-methanesulfonamide

Produkt 1

HCID 24802657HCID 24802657, VerbindungAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 0.050 g (0.39 mmol) of 4-nitro-2H-pyrazol-3-ylamine and 0.124 g (0.39 mmol) of N-[5-(3-dimethylamino-acryloyl)-2-chloro-phenyl]-N-methyl-methanesulfonamide in 12 mL of glacial acetic acid was refluxed for 1.5 hours and then the solvent was removed by reduced pressure distillation. To the resulting residue were added 15 mL of dichloromethane and 10 mL of saturated sodium bicarbonate solution. The two layers were separated, and the aqueous layer was washed with 10 mL of dichloromethane. The organic layers were washed with 10 mL of water and dried over magnesium sulfate. The dichloromethane layer was evaporated to dryness to yield an oil which, in the presence of ethyl acetate, gave 56 mg of N-{2-chloro-5-[3-nitro-pyrazolo[1,5-a]pyrimidin-7-yl]-phenyl}-N-methyl-methanesulfonamide as a solid (yield 77%).

Aufarbeitung

  1. temperaturewas refluxed for 1.5 hours
  2. customthe solvent was removed by reduced pressure distillation
  3. additionTo the resulting residue were added 15 mL of dichloromethane and 10 mL of saturated sodium bicarbonate solution
  4. customThe two layers were separated
  5. washthe aqueous layer was washed with 10 mL of dichloromethane
  6. washThe organic layers were washed with 10 mL of water
  7. dry with materialdried over magnesium sulfate
  8. customThe dichloromethane layer was evaporated to dryness
  9. customto yield an oil which

Quellen und Nachweise

ORD-Eintrag
ord-fd12456d62f7493e9bd8adc9e6e4a88c
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158632B2

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