m-Chloroperbenzoic acid → (+/-)-1-(Oxiranylmethyl)-2,4-imidazolidinedione

HRID 917288

Reaction equation

HRID 917288 reaction equation
[CH2:1]([N:4]1[CH2:8][C:7](=[O:9])[NH:6][C:5]1=[O:10])[CH:2]=[CH2:3].ClC1C=C(C(OO)=[O:19])C=CC=1.S(=O)(O)[O-]>C(Cl)Cl>[O:19]1[CH2:3][CH:2]1[CH2:1][N:4]1[CH2:8][C:7](=[O:9])[NH:6][C:5]1=[O:10]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 104748BisulfiteHCID 220209241-(Prop-2-en-1-yl)imidazolidine-2,4-dione

Product 1

HCID 22020929(+/-)-1-(Oxiranylmethyl)-2,4-imidazolidinedioneYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A reaction solution of 1-(2-propenyl)-2,4-imidazolidinedione (0.036 mol) and 3-chloro-benzenecarboperoxoic acid (0.043 mol, 70.75%) in DCM (25 ml) was stirred for 2 hours at room temperature. An aqueous solution of bisulfite was added (to remove excess 3-chlorobenzenecarboperoxoic acid) and the mixture was stirred for 10 minutes. Na2CO3 was added and this mixture was extracted with DCM. The separated organic layer was dried, filtered and the solvent evaporated, yielding 5 g (89%) of (±)-1-(oxiranylmethyl)-2,4-imidazolidinedione (interm. 1).

Workup

  1. custom(to remove excess 3-chlorobenzenecarboperoxoic acid)
  2. additionNa2CO3 was added
  3. extractionthis mixture was extracted with DCM
  4. customThe separated organic layer was dried
  5. filtrationfiltered
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-7944daf78bd94ed1bbf1d811cb1457ed
Source dataset
uspto-grants-2007_09
Patent number
US07273862B2

Linked notes

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