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Ethylenediamine → 5-Cyano-2-(2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole

HRID 37576
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 37576
Br[C:2]1[CH:19]=[CH:18][C:5]2[O:6][C:7]([CH2:13][C:14]([F:17])([F:16])[F:15])([C:9]([F:12])([F:11])[F:10])[O:8][C:4]=2[CH:3]=1.[Cu][C:21]#[N:22].NCCN>CN(C)C=O>[C:21]([C:2]1[CH:19]=[CH:18][C:5]2[O:6][C:7]([CH2:13][C:14]([F:17])([F:16])[F:15])([C:9]([F:12])([F:11])[F:10])[O:8][C:4]=2[CH:3]=1)#[N:22]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 3301EthylenediamineHCID 189959475-Bromo-2-(2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxoleHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 189959435-Cyano-2-(2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxoleAusbeute 69,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

35 g of the product of Example 24 were dissolved in 75 ml of dimethylformamide, and 10.5 g of copper(I) cyanide were added. The mixture was stirred for 8 hours at 160° C. The hot mixture was then discharged into 100 ml of ice-water, and 30 g of 1,2-diaminoethane were added. After stirring for 30 minutes, the organic phase was separated off and the aqueous phase was extracted with methylene chloride. The combined organic phases were washed with a solution of 30 g of 1,2-diaminoethane in 75 ml of water, dried over magnesium sulphate and distilled under high vacuum to give 20.5 g of product (=69% of theory). The. boiling point was 110° C. at 0.02 mbar. =19F NMR: -58.1 and -84.6 ppm. 1H NMR: 3.08 ppm.

Aufarbeitung

  1. additionwere added
  2. stirringAfter stirring for 30 minutes
  3. customthe organic phase was separated off
  4. extractionthe aqueous phase was extracted with methylene chloride
  5. washThe combined organic phases were washed with a solution of 30 g of 1,2-diaminoethane in 75 ml of water
  6. dry with materialdried over magnesium sulphate
  7. distillationdistilled under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-3b6125c7f4fe4b728e99433e566e92b2
Quelldatensatz
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05420309

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