Sodium Carbonate → 2-[N-(cyclopropyl-methyl)-N-(2,6-dichloro-phenyl)-amino]-2-imidazoline

HRID 866642Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 866642
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]=[C:10]1[NH:14][CH2:13][CH2:12][NH:11]1.Cl[CH2:16][CH:17]1[CH2:19][CH2:18]1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[CH:17]1([CH2:16][N:9]([C:10]2[NH:14][CH2:13][CH2:12][N:11]=2)[C:3]2[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[CH2:19][CH2:18]1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 80013(Chloromethyl)cyclopropaneHCID 178478105HCID 178478105, Verbindung

Produkt 1

HCID 126746362-[N-(cyclopropyl-methyl)-N-(2,6-dichloro-phenyl)-amino]-2-imidazolineAusbeute 10,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture consisting of 6.9 gm (0.03 mol) of 2-(2,6-dichlorophenyl-imino)-imidazolidine, 2.9 gm (110% of stoichiometrically required amount) or chloromethyl-cyclopropane, 4 gm of sodium carbonate and 50 ml of absolute toluene was refluxed for 32 hours, while stirring. Thereafter, the reaction solution was evaporated to dryness in vacuo, and the residue was dissolved in about 1N hydrochloric acid. The resulting acidic solution was extracted several times with ether, and the ethereal extracts were discarded. The acidic aqueous phase was then fractionally extrated with ether at stepwisely increasing pH-values (alkalization with dilute sodium hydroxide), and the thin-layer chromatographically pure fractions were combined, dried over magnesium sulfate and evaporated in vacuo, yielding as the residue 0.9 gm (10.6% of theory) of the compound of the formula ##STR7## which had a melting point of 126°-129° C.

Aufarbeitung

  1. temperaturewas refluxed for 32 hours
  2. customThereafter, the reaction solution was evaporated to dryness in vacuo
  3. dissolutionthe residue was dissolved in about 1N hydrochloric acid
  4. extractionThe resulting acidic solution was extracted several times with ether
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cabc52577d804c58adbb828bfc8707c3
Quelldatensatz
uspto-grants-1978_07
Patentnummer
US04100292

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