Ethyl Acetate → (+/-)-1,1-dimethyl-1a,3,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carbonitrile

HRID 1295069Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1295069
[CH3:1][C:2]1([CH3:14])[CH:4]2[CH2:5][C:6]3[C:10]([CH:3]12)=[N:9][NH:8][C:7]=3[C:11]([NH2:13])=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(OCC)(=O)C>C1COCC1>[CH3:1][C:2]1([CH3:14])[CH:4]2[CH2:5][C:6]3[C:10]([CH:3]12)=[N:9][NH:8][C:7]=3[C:11]#[N:13]

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 9845Trifluoroacetic anhydrideHCID 178421816HCID 178421816, Verbindung

Produkt 1

HCID 178421815(+/-)-1,1-dimethyl-1a,3,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(±)-1,1-Dimethyl-1a,3,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid amide (0.532 g, 2.79 mmol) was taken up in THF (150 mL) and trifluoroacetic anhydride (0.936 g, 4.46 mmol) added. The resulting solution was stirred at room temperature under argon for 1 hour. Ethyl acetate (50 mL) was added and solvent removed under reduced pressure. The resulting pale yellow oil was taken up in DCM (100 mL), washed with saturated aqueous sodium bicarbonate solution (40 mL) and solvent removed under reduced pressure. The resulting white solid was taken up as a suspension in DCM (20 mL) and filtered to give (±)-1,1-dimethyl-1a,3,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carbonitrile as an off-white solid. m/z (ES): 174 [M+H]+

Aufarbeitung

  1. customsolvent removed under reduced pressure
  2. washwashed with saturated aqueous sodium bicarbonate solution (40 mL) and solvent
  3. customremoved under reduced pressure
  4. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-d0c8b36b36ee4018a8bd67a11aee76d4
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07241792B2

Notizen zur Reaktion

Wird geladen…