Dimethylhydantoin → HCID 20530782, compound

HRID 1833392Notes

Reaction equation

HRID 1833392 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:14]=1[OH:15])[CH2:8][CH:9]1[CH2:11][O:10]1)([CH3:4])([CH3:3])[CH3:2].[CH3:20][C:21]1([CH3:28])[NH:25][C:24](=[O:26])[NH:23][C:22]1=[O:27]>[Cl-].[Li+]>[OH:10][CH:9]([CH2:8][C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:14]([OH:15])=[C:13]([C:16]([CH3:19])([CH3:17])[CH3:18])[CH:12]=1)[CH2:11][N:23]1[C:22](=[O:27])[C:21]([CH3:28])([CH3:20])[NH:25][C:24]1=[O:26]

Participants

4

Reactant 2

HCID 6491DimethylhydantoinHCID 20530805HCID 20530805, compound

Product 1

HCID 20530782HCID 20530782, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 433294Lithium ChlorideCatalyst

Procedure

25 mg of lithium chloride are added to 5.25 g (0.02 mol) of 3,5-di-tert.-butyl-4-hydroxybenzyl-oxirane and 2.56 g (0.02 mol) of 5,5-dimethylhydantoin and the mixture is kept at a melt at 220°-230° C for 60 minutes whilst stirring in a nitrogen atmosphere. After cooling, a glassy residue is obtained, which when recrystallised from toluene/isopropanol gives 6.2 g (78% of theory) of 3-[2-hydroxy-3-(3,5-di-tert.-butyl-4-hydroxyphenyl)-propyl]-5,5-dimethylhydantoin of melting point 175°-76° C in the form of colourless crystals.

Workup

  1. temperatureAfter cooling
  2. customa glassy residue is obtained
  3. customwhich when recrystallised from toluene/isopropanol

Sources & evidence

ORD record
ord-f1baf17e7fa643c99257f8d2963281ec
Source dataset
uspto-grants-1978_01
Patent number
US04066616

Reaction notes

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