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

HRID 461534Notes

Reaction equation

HRID 461534 reaction equation
[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]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 728231-Aminohydantoin

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-c4cc6d670166462285eaefd03e7c900b
Source dataset
uspto-grants-1977_12
Patent number
US04063019

Reaction notes

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