Dimethylformamide → 2,4-Imidazolidinedione, 3-[(4-chlorophenyl)methyl]-

HRID 896996Notes

Reaction equation

HRID 896996 reaction equation
[K].[NH:2]1[CH2:6][C:5](=[O:7])[NH:4][C:3]1=[O:8].[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Br)=[CH:12][CH:11]=1.CN(C)C=O>O>[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][N:4]2[C:5](=[O:7])[CH2:6][NH:2][C:3]2=[O:8])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10006HydantoinHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 5462222Potassium

Product 1

HCID 10851902,4-Imidazolidinedione, 3-[(4-chlorophenyl)methyl]-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
172.5 °C

Procedure

Under a nitrogen atmosphere in a flame-dried flask, with magnetic stirring, the potassium salt of imidazolidine-2,4-dione (1.382 g, 10 mmol) and 4-chlorobenzyl bromide (2.055 g, 10 mmol) were combined with 15 mL of anhydrous N,N-dimethylformamide (DMF) and heated to 170-175° C. for 5 hours. The reaction was then cooled to room temperature and poured over 50 mL of water to produce a waxy white precipitate. Recrystallization from ethyl acetate: hexanes produced the title product as a white crystalline solid, 0.775 g (34.5%).

Workup

  1. temperatureThe reaction was then cooled to room temperature
  2. customto produce a waxy white precipitate
  3. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-443c67e39e164ddbbda4ceab74791db3
Source dataset
uspto-grants-2005_07
Patent number
US06921760B2

Reaction notes

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