Phosgene → (2,4-Dioxoimidazolidin-1-yl)carbamyl chloride

HRID 461534

Reaktionsgleichung

Reaktionsgleichung von HRID 461534
[NH2:1][N:2]1[CH2:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].[C:9](Cl)([Cl:11])=[O:10]>O1CCCC1>[Cl:11][C:9]([NH:1][N:2]1[CH2:6][C:5](=[O:7])[NH:4][C:3]1=[O:8])=[O:10]

Komponenten

4

Edukt 2

HCID 6371PhosgeneHCID 728231-Aminohydantoin

Produkt 1

HCID 20325743(2,4-Dioxoimidazolidin-1-yl)carbamyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

11.5 g. (0.1 mol.) of 1-amino-2,4-dioxoimidazolidine are thoroughly stirred into 150 ml. of absolute tetrahydrofuran. A solution of 15 g. (0.15 mol.) of phosgene in 25 ml. of absolute tetrahydrofuran is added dropwise at 0°-5° over 20 minutes. The mixture is then stirred for 3 hours at room temperature. An almost clear solution results. This is filtered and the solvent is evaporated in vacuum. The oily residue crystallizes on trituration with petroleum ether to obtain 1-(chlorocarbonylamino)-2,4-dioxoimidazolidine, yield 17.2 g., m.p. 126° (dec.).

Aufarbeitung

  1. customAn almost clear solution results
  2. filtrationThis is filtered
  3. customthe solvent is evaporated in vacuum
  4. customThe oily residue crystallizes on trituration with petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-c4cc6d670166462285eaefd03e7c900b
Quelldatensatz
uspto-grants-1977_12
Patentnummer
US04063019

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