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

HRID 2413386Notes

Reaction equation

HRID 2413386 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]=CC=C[CH:28]=1.S(=O)(=O)(O)O.[CH2:38](O)[CH2:39][CH3:40]>>[CH2:19]([N:10]1[C@H:11]([C:16]([O:18][CH2:28][CH2:27][CH3:32])=[O:17])[C@H:12]([C:13]([O:15][CH2:38][CH2:39][CH3:40])=[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 4

HCID 241BenzeneHCID 10311-PropanolHCID 1118Sulfuric AcidHCID 9841512cis-1,3-Dibenzyl-2-imidazolidone-4,5-dicarboxylic acid

Product 1

HCID 18595938Di-n-propyl 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), n-propanol (45 ml) and conc. sulfuric acid (5.0 g) was refluxed for 14 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-propyl cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylate (42.3 g). IR (neat, cm-1): 2970, 1750, 1710, 1445, 1420, 1360, 1210, 1055, 750, 700.

Workup

  1. temperaturewas refluxed for 14 hours
  2. temperaturecooled
  3. washwashed successively with water, 5% aqueous sodium hydroxide and water
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c5f1a7ffed724913be3a14087f8f16f4
Source dataset
uspto-grants-1985_01
Patent number
US04496739

Reaction notes

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