Acetic Anhydride → HCID 15871313, Verbindung

HRID 612982

Reaktionsgleichung

Reaktionsgleichung von HRID 612982
CC1C=CC(C)=CC=1C(CC#N)=O.COC(OC)(OC)CCC.C(OC(=O)C)(=O)C.[C:31]([C:33]([C:40](=[O:49])[C:41]1[CH:46]=[C:45]([CH3:47])[CH:44]=[CH:43][C:42]=1[CH3:48])=[CH:34][CH:35](OC)[CH2:36][CH3:37])#[N:32].C(N(CC)CC)C.[Cl:57][C:58]1[CH:63]=[C:62]([C:64]([F:67])([F:66])[F:65])[CH:61]=[C:60]([Cl:68])[C:59]=1[NH:69][NH2:70]>C(OCC)(=O)C>[NH2:32][C:31]1[N:69]([C:59]2[C:60]([Cl:68])=[CH:61][C:62]([C:64]([F:65])([F:66])[F:67])=[CH:63][C:58]=2[Cl:57])[N:70]=[C:34]([CH2:35][CH2:36][CH3:37])[C:33]=1[C:40](=[O:49])[C:41]1[CH:46]=[C:45]([CH3:47])[CH:44]=[CH:43][C:42]=1[CH3:48]

Komponenten

8

Edukt 6

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 1235121,1,1-TrimethoxybutaneHCID 688223[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazineHCID 158952643-(2,5-Dimethylphenyl)-3-oxopropanenitrileHCID 536488461-Cyano-1-(2,5-dimethylbenzoyl)-3-methoxy-1-pentene

Produkt 1

HCID 15871313HCID 15871313, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 0.52 g (3.0 mmol) of 2,5-dimethylbenzoylacetonitrile, 0.45 g (3.0 mmol) of trimethylorthobutyrate and 0.632 g (0.58 mL, 6.2 mmol) of acetic anhydride in 5.0 mL of ethyl acetate was refluxed overnight and then cooled. The solvents were removed in vacuo and the residues were dissolved in 10 mL of ethanol. One-half of this solution, containing 1.5 mmol of 1 -cyano-1 -(2,5-dimethylbenzoyl)-3-methoxy-1-pentene was mixed with 0.7 mL (0.51 g, 5.0 mmol) of triethylamine and 0.37 g (1.50 mmol) of 2,6-dichloro-4-trifluoromethylphenylhydrazine and refluxed for 2.5 hours. The reaction mixture was cooled and partitioned between dilute hydrogen chloride and ethyl acetate. The organic phase was washed with water and then dried with brine and with magnesium sulfate. The solvent was evaporated to give an oil which was chromatographed on silica gel by the flash method eluting with 4:1 hexane/ethyl acetate to give the title compound as an amorphous foam. Anal. Calcd. for C22H20ON3Cl2F3, 469.0935. Found: 469.0889.

Aufarbeitung

  1. temperaturecooled
  2. customThe solvents were removed in vacuo
  3. dissolutionthe residues were dissolved in 10 mL of ethanol
  4. temperaturerefluxed for 2.5 hours
  5. temperatureThe reaction mixture was cooled
  6. custompartitioned between dilute hydrogen chloride and ethyl acetate
  7. washThe organic phase was washed with water
  8. dry with materialdried with brine and with magnesium sulfate
  9. customThe solvent was evaporated
  10. customto give an oil which
  11. customwas chromatographed on silica gel by the flash method
  12. washeluting with 4:1 hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-9246fe02c12d4ba2b785b0bc098d3e87
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06005109

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