Chloroform → 2-Benzoyl-3-dimethylaminocrotononitrile

HRID 128172

Reaktionsgleichung

Reaktionsgleichung von HRID 128172
[C:1]([CH2:9][C:10]#[N:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(Cl)Cl.CO[C:18](OC)([N:20]([CH3:22])[CH3:21])[CH3:19]>C1C=CC=CC=1>[C:1](/[C:9](=[C:18](/[N:20]([CH3:22])[CH3:21])\[CH3:19])/[C:10]#[N:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 6212Chloroform2×HCID 64799BenzoylacetonitrileHCID 878351,1-Dimethoxyethyl(dimethyl)amine

Produkt 1

HCID 146739772-Benzoyl-3-dimethylaminocrotononitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

To a solution of 14.5 g. (0.10 m) of benzoylacetonitrile in 100 ml. of chloroform, cooled in an ice-salt bath, was added 13.3 g. (0.1 m) of N,N-dimethylacetamide dimethylacetal in 20 ml. chloroform. The reaction mixture was stirred in the ice-salt bath for 2 hours, then evaporated in vacuo to an orange oil. The oil was dissolved in 150 ml. benzene and passed through Magnesol®. The filtrate was evaporated and the oil thus obtained was dissolved in 50 ml. benzene to which pet ether was added until the solution became cloudy. The precipitate which formed upon cooling was collected. The solid was recrystallized twice from benzene-pet ether, with charcoal treatment to yield 5.8 g. (27%) of light yellow crystals, m.p. 105°-106° C.

Aufarbeitung

  1. additionwas added 13.3 g
  2. customevaporated in vacuo to an orange oil
  3. dissolutionThe oil was dissolved in 150 ml
  4. customThe filtrate was evaporated
  5. customthe oil thus obtained
  6. dissolutionwas dissolved in 50 ml
  7. customThe precipitate which formed
  8. temperatureupon cooling
  9. customwas collected
  10. customThe solid was recrystallized twice from benzene-pet ether, with charcoal treatment
  11. customto yield 5.8 g

Quellen und Nachweise

ORD-Eintrag
ord-084c675acf0944cf8cdefa7dd2e4ae02
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04259256

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