4-[(2,5-Dioxoimidazolidin-1-yl)methyl]benzonitrile → 3-(4-Formylbenzyl)hydantoin

HRID 433222Notes

Reaction equation

[C:1]([C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[C:12](=[O:13])[CH2:11][NH:10][C:9]2=[O:14])=[CH:5][CH:4]=1)#N.[PH2]([O-])=[O:18].[Na+]>N1C=CC=CC=1.C(O)(=O)C.O.[Ni]>[CH:1]([C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[C:12](=[O:13])[CH2:11][NH:10][C:9]2=[O:14])=[CH:5][CH:4]=1)=[O:18]

Participants

Conditions

Temperature: 0 °C

Procedure

The 3-(4-cyanobenzyl)hydantoin derivative obtained in step F (about 14 mmol) was dissolved in 360 ml of a mixture of pyridine/acetic acid/water (2/1/1), cooled to 0° C. and treated with 25.1 g of sodium hypophosphite (monohydrate) and 4.17 g of moist Raney nickel. After stirring at 60° C. for 6 h, the solvents were removed in vacuo and the residue was taken up in ethyl acetate. The solvent was washed with 10% strength citric acid solution, saturated sodium bicarbonate solution and saturated sodium chloride solution and dried over magnesium sulfate. After filtration and concentration, the 3-(4-formylbenzyl)hydantoin derivative obtained was employed in the next step without further purification.

Workup

customthe solvents were removed in vacuo
washThe solvent was washed with 10% strength citric acid solution, saturated sodium bicarbonate solution and saturated sodium chloride solution
dry with materialdried over magnesium sulfate
filtrationAfter filtration and concentration

Sources & evidence

ORD record: ord-5e927dba59bc42b0832fb1ce884b1a2d
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06667334B1

Reaction notes

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