Benzene → Diethyl cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylate

HRID 2413384Notes

Reaction equation

[CH2:1]([N:8]1[C@H:12]([C:13]([OH:15])=[O:14])[C@H:11]([C:16]([OH:18])=[O:17])[N:10]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:9]1=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:27]1C=CC=C[CH:28]=1.S(=O)(=O)(O)O.[CH2:38](O)[CH3:39]>>[CH2:19]([N:10]1[C@H:11]([C:16]([O:18][CH2:27][CH3:28])=[O:17])[C@H:12]([C:13]([O:15][CH2:38][CH3:39])=[O:14])[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]1=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Reactant 4

HCID 241Benzene

HCID 702Ethanol

HCID 1118Sulfuric Acid

HCID 9841512cis-1,3-Dibenzyl-2-imidazolidone-4,5-dicarboxylic acid

Product 1

HCID 13276246Diethyl cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylate

Procedure

A mixture of cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid (35.4 g), benzene (500 ml), 9.5% ethanol (45 ml) and conc. sulfuric acid (5.0 g) was refluxed for 10 hours, cooled, washed successively with water, 5% aqueous sodium hydroxide and water, and then concentrated under reduced pressure. The residue was recrystallized from 95% ethanol to give diethyl cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylate (32.1 g). M.P., 74°-76° C.

Workup

temperaturewas refluxed for 10 hours
temperaturecooled
washwashed successively with water, 5% aqueous sodium hydroxide and water
concentrationconcentrated under reduced pressure
customThe residue was recrystallized from 95% ethanol

Sources & evidence

ORD record: ord-4f91325d1c99433ca5639644a23fc0dd
Source dataset: uspto-grants-1985_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04496739

Reaction notes

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