Sodium Carbonate → (+/-)-1-(Oxiranylmethyl)-2,4-imidazolidinedione

HRID 30091

Reaction equation

HRID 30091 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([O-])([O-])=O.[Na+].[Na+]>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

6

Reactant 4

HCID 10340Sodium CarbonateHCID 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 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 of (±)-1-(oxiranylmethyl)-2,4-imidazolidinedione (intermediate 18).

Workup

  1. extractionthis mixture was extracted with DCM
  2. customThe separated organic layer was dried
  3. filtrationfiltered
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-2d6311f3fe124212b3572c7a948ab5ac
Source dataset
uspto-grants-2008_09
Patent number
US07423048B2

Linked notes

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