Benzene → Di-n-butyl cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylate

HRID 463732Notes

Reaction equation

HRID 463732 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]1[CH:32]=[CH:31][CH:30]=CC=1.S(=O)(=O)(O)O>C(O)CCC>[CH2:19]([N:10]1[C@H:11]([C:16]([O:18][CH2:1][CH2:2][CH2:3][CH3:4])=[O:17])[C@H:12]([C:13]([O:15][CH2:27][CH2:32][CH2:31][CH3:30])=[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

5

Reactant 3

HCID 241BenzeneHCID 1118Sulfuric AcidHCID 9841512cis-1,3-Dibenzyl-2-imidazolidone-4,5-dicarboxylic acid

Product 1

HCID 18595937Di-n-butyl cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylate

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid (35.4 g), benzene (500 ml), n-butanol (45 ml) and conc. sulfuric acid (5.0 g) was refluxed for 16 hours, cooled, washed successively with water, 5% aqueous sodium hydroxide and water, and then concentrated under reduced pressure to give oily product of di-n-butyl cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylate (39.5 g). IR (neat, cm-1): 2950, 1750, 1710, 1445, 1420, 1350, 1200, 1060, 1020, 960, 745, 695.

Workup

  1. temperaturewas refluxed for 16 hours
  2. temperaturecooled
  3. washwashed successively with water, 5% aqueous sodium hydroxide and water
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fe50e4aa99d14c408e7a15e6b4c3a33e
Source dataset
uspto-grants-1985_10
Patent number
US04544635

Reaction notes

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