3,5-Dichlorophenyl isocyanate → 3-(3,5-Dichlorophenyl)-5-methyl-1-(prop-2-yn-1-yl)imidazolidine-2,4-dione

HRID 2226162Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2226162
[CH2:1]([NH:4][CH:5]([CH3:10])[C:6]([O:8]C)=O)[C:2]#[CH:3].[Cl:11][C:12]1[CH:13]=[C:14]([N:19]=[C:20]=[O:21])[CH:15]=[C:16]([Cl:18])[CH:17]=1>C1(C)C=CC=CC=1>[CH2:1]([N:4]1[CH:5]([CH3:10])[C:6](=[O:8])[N:19]([C:14]2[CH:15]=[C:16]([Cl:18])[CH:17]=[C:12]([Cl:11])[CH:13]=2)[C:20]1=[O:21])[C:2]#[CH:3]

Komponenten

4

Edukt 2

HCID 944603,5-Dichlorophenyl isocyanateHCID 14326200HCID 14326200, Verbindung

Produkt 1

HCID 143262013-(3,5-Dichlorophenyl)-5-methyl-1-(prop-2-yn-1-yl)imidazolidine-2,4-dioneAusbeute 86,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of methyl 2-propargylaminopropionate (10 g, 0.07 mole) in toluene (100 mL) with 2 drops of stannous octonoate was added 3,5-dichlorophenylisocyanate (14.5 g, 0,077 mole) in small portions. The resulting mixture was heated at 100° C. for 3 hours. It was then washed with water twice and dried over sodium sulfate. Solvent was evaporated to give a thick, yellow oil. Material was further purified by passing it through a silica gel column using 30/70 ethyl acetate/hexane as eluent to give 18 grams of a light yellow oil which solidified on standing. The solids were triturated in boiling hexane and collected by suction filtration; mp 105°-106° C., NMR and elemental analysis confirmed the desired structure.

Aufarbeitung

  1. washIt was then washed with water twice
  2. dry with materialdried over sodium sulfate
  3. customSolvent was evaporated
  4. customto give a thick, yellow oil
  5. customMaterial was further purified

Quellen und Nachweise

ORD-Eintrag
ord-12059fc4cbf04792b4d452cf1c098e29
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05346913

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