1,2-Dichlorobenzene → 2-((4-Chlorophenoxy)methyl)-2-imidazoline hydrochloride

HRID 66729

Reaktionsgleichung

Reaktionsgleichung von HRID 66729
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][C:8]#[N:9])=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:23](N)[CH2:24][NH2:25].ClC1C=CC=CC=1Cl>C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][C:8]2[NH:25][CH2:24][CH2:23][N:9]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 72391,2-DichlorobenzeneHCID 2250301,2-Ethanediamine, 4-methylbenzenesulfonate (1:?)HCID 3064442-(4-Chlorophenoxy)acetonitrile

Produkt 1

HCID 205290632-((4-Chlorophenoxy)methyl)-2-imidazoline hydrochlorideAusbeute 148,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
178 °C

Versuchsvorschrift

A mixture of 25.1 g of 4-chlorophenoxyacetonitrile, 35.0 g of ethylenediamine p-toluenesulfonate and 112.5 ml of 1,2-dichlorobenzene was heated with stirring in a 500 ml round-bottomed three-necked flask at reflux (178° C.) for 1.0 hour. The reaction mixture was cooled, then diluted with methylene chloride and filtered. The crystals that were obtained were dried in a vacuum oven. The dried crystals were slurried in water, the resulting slurry basified and then extracted with methylene chloride. The methylene chloride extract was treated with diatomaceous earth and activated charcoal and then filtered. The methylene chloride was evaporated and 27.4 g of the free imidazoline obtained, m.p. 116°-118° C. The free imidazoline was then put in solution in isopropyl alcohol and acidified with HCl in isopropyl alcohol. The mixture was then cooled and filtered which gave 27.4 g of 2-((4-chlorophenoxy)methyl)-2-imidazoline hydrochloride, m.p. 185°-186° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. customThe crystals that were obtained
  5. customwere dried in a vacuum oven
  6. extractionextracted with methylene chloride
  7. extractionThe methylene chloride extract
  8. additionwas treated with diatomaceous earth and activated charcoal
  9. filtrationfiltered
  10. customThe methylene chloride was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-df29524393e74970aa34b15ba66ebab5
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04343809

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