Acetic Anhydride → 5-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-(2,5-dimethylbenzoyl)-3-ethoxypyrazole

HRID 1871619

Reaktionsgleichung

Reaktionsgleichung von HRID 1871619
[CH3:1][C:2]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:3]=1[C:4]([CH2:6][C:7]#[N:8])=[O:5].C(O[C:17]([O:24][CH2:25][CH3:26])(OCC)OCC)C.C(OC(=O)C)(=O)C.[Cl:34][C:35]1[CH:40]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:38]=[C:37]([Cl:45])[C:36]=1[NH:46][NH2:47].C(N(CC)CC)C>CCOC(C)=O.O>[NH2:8][C:7]1[N:46]([C:36]2[C:37]([Cl:45])=[CH:38][C:39]([C:41]([F:42])([F:43])[F:44])=[CH:40][C:35]=2[Cl:34])[N:47]=[C:17]([O:24][CH2:25][CH3:26])[C:6]=1[C:4](=[O:5])[C:3]1[CH:9]=[C:10]([CH3:13])[CH:11]=[CH:12][C:2]=1[CH3:1]

Komponenten

8

Edukt 5

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 66213Tetraethyl orthocarbonateHCID 688223[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazineHCID 158952642,5-Dimethylbenzoylacetonitrile

Produkt 1

HCID 129721435-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-(2,5-dimethylbenzoyl)-3-ethoxypyrazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 0.26 g (1.5 mmol) of 2,5-dimethylbenzoylacetonitrile, 0.34 mL (0.31 g, 1.60 mmol) of tetraethylorthocarbonate and 0.30 mL (0.33 g, 3.20 mmol) of acetic anhydride in 10 mL of EtOAc was refluxed overnight. The solvent was evaporated and 10 mL of absolute ethanol was added and then stripped. The residues were dissolved in 10 mL of ethanol, 368 mg (1.5 mmol) of 2,6-dichloro-4-trifluoromethylphenyl-hydrazine and 0.7 mL (0.51 g, 5.0 mmol) of triethylamine were added, and the mixture was refluxed for 90 minutes. The mixture was poured into water, extracted with EtOAc and the organic extracts were washed with dilute HCL and brine, and dried over MgSO4. Evaporation gave a gum which was chromatographed on silica gel with 4:1 hexane/EtOAc to give the title product which crystallized from pentane, 15 mg (2%), m.p. 99-101° C.

Aufarbeitung

  1. customThe solvent was evaporated
  2. addition10 mL of absolute ethanol was added
  3. dissolutionThe residues were dissolved in 10 mL of ethanol
  4. temperaturethe mixture was refluxed for 90 minutes
  5. extractionextracted with EtOAc
  6. washthe organic extracts were washed with dilute HCL and brine
  7. dry with materialdried over MgSO4
  8. customEvaporation
  9. customgave a gum which
  10. customwas chromatographed on silica gel with 4:1 hexane/EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-ca9e5207d5f14bdabc8e5e3d54ce5d4e
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06103900

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