1,1'-Carbonyldiimidazole → 1-[(4-Bromophenyl)methyl]imidazolidine-2,4-dione

HRID 1891254Notes

Reaction equation

HRID 1891254 reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][NH:7][CH2:8][C:9]([NH2:11])=[O:10])=[CH:4][CH:3]=1.[C:14](N1C=CN=C1)(N1C=CN=C1)=[O:15]>C(#N)C.CN(C)C1C=CN=CC=1.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:8][C:9](=[O:10])[NH:11][C:14]2=[O:15])=[CH:12][CH:13]=1

Participants

6

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 167779692-((4-Bromobenzyl)amino)acetamide

Product 1

HCID 154067221-[(4-Bromophenyl)methyl]imidazolidine-2,4-dioneYield 20.6%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2-(4-bromobenzylamino)acetamide (1B3) (45.9 mmol, 11.2 g) and carbonyldiimidazole (68.8 mmol, 11.2 g) in acetonitrile (223 ml) was cooled to 0° C. with stirring and 4-dimethylaminopyridine (45.9 mmol, 5.60 g) was added. The mixture was stirred at 0° C. for 24 h and then heated at 80° C. for 18 h. The reaction mixture was diluted with water and the acetonitrile removed under reduced pressure. The mixture was acidified to pH 4 with aqueous HCl and the precipitate collected by filtration and dried in a vacuum oven to give 1-(4-bromobenzyl)imidazolidine-2,4-dione (1B4) 2.55 g (20.2%); 1H NMR (400 MHz, DMSOd6) δ 10.94 (bs, NH) 7.55 (d, 2H) 7.24 (d, 2H) 4.42 (s, 2H) 3.86 (s, 2H).

Workup

  1. stirringThe mixture was stirred at 0° C. for 24 h
  2. temperatureheated at 80° C. for 18 h
  3. customthe acetonitrile removed under reduced pressure
  4. filtrationthe precipitate collected by filtration
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-4e25ff0a59df49f5a87ceefeac34adf1
Source dataset
uspto-grants-2013_08
Patent number
US08507521B2

Reaction notes

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