HCID 21388924, compound → HCID 21401467, compound

HRID 973148Notes

Reaction equation

HRID 973148 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]2[C:16](=[O:17])[C:15](=[O:18])[N:14]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]([O:28][CH3:29])=[O:27])=[CH:22][CH:21]=3)[C:13]2([CH3:31])[CH3:30])=[CH:7][CH:6]=1)=[O:4]>C(O)CCC.[Ti].CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4]>[CH2:29]([O:28][C:26]([C:23]1[CH:24]=[CH:25][C:20]([CH2:19][N:14]2[C:15](=[O:18])[C:16](=[O:17])[N:12]([CH2:11][C:8]3[CH:9]=[CH:10][C:5]([C:3]([O:2][CH2:1][CH2:7][CH2:8][CH3:9])=[O:4])=[CH:6][CH:7]=3)[C:13]2([CH3:31])[CH3:30])=[CH:21][CH:22]=1)=[O:27])[CH2:3][CH2:5][CH3:6]

Participants

5

Reactant 1

HCID 21388924HCID 21388924, compound

Product 1

HCID 21401467HCID 21401467, compoundYield 140%

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 23963TitaniumCatalystHCID 2631-ButanolSolvent

Procedure

5 g (0.0118 mole) of 1,3-bis-(4'-methoxycarbonylphenylmethyl)-2,2-dimethylimidazolidine-4,5-dione, with the addition of 0.01% of titanium as titanium tetraisopropylate, are refluxed for 2 hours in n-butanol. The methanol which forms is distilled off continuously. The colourless crystals which precipitate after the reaction mixture has cooled are collected by suction filtration and recrystallised from n-butanol to yield 4.2 g of colourless crystals with a melting point of 111°-112° C. The IR and NMR spectra confirm the presumed structure.

Workup

  1. distillationThe methanol which forms is distilled off continuously
  2. customThe colourless crystals which precipitate after the reaction mixture
  3. temperaturehas cooled
  4. filtrationare collected by suction filtration
  5. customrecrystallised from n-butanol

Sources & evidence

ORD record
ord-4e38a6e03a8c4a33a85032d196870890
Source dataset
uspto-grants-1977_10
Patent number
US04055570

Reaction notes

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