HCID 275570, compound → HCID 20215477, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[C:15]([O:19][CH3:20])[C:16]=1[O:17][CH3:18])[CH:6]=[C:7]1[NH:11][C:10](=[O:12])[NH:9][C:8]1=[O:13]>[Ni].[Pd]>[CH3:20][O:19][C:15]1[CH:14]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:16]=1[O:17][CH3:18])[CH2:6][CH:7]1[NH:11][C:10](=[O:12])[NH:9][C:8]1=[O:13]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
boiling an aqueous solution of glycine and urea in a molar ratio of 1:1.8 to 1:5 to form hydantoic acid as an intermediate, and directly cyclizing the hydantoic acid intermediate by adding to the solution concentrated sulfuric acid in a molar ratio of 1:0.3 to 1:1 relative to the glycine to form hydantoin of the Formula (I) as a precipitate and a mother liquor: ##STR8## and separating the precipitate of hydantoin from the mother liquor; (b) condensing the hydantoin formed during step (a) with an aromatic aldehyde of the Formula (II) ##STR9## in an aqueous solution in the presence of ethanolamine or morpholine to obtain a 5-arylidene-methyl-hydantoin of the Formula (III) ##STR10## (c) quantitatively reducing the compound of the Formula (III) prepared in step (b) in a diluted alkaline medium in the presence of a Raney nickel or palladium-on-charcoal catalyst, to obtain a 5-aryl-methyl-hydantoin of the Formula (IV) ##STR11## and; (d) subjecting the compound of the Formula (IV) to alkaline hydrolysis to yield the compound of the Formula (V).
Sources & evidence
- ORD record
- ord-3f7ea91de02c45e9bee1c84a78b5c0f9
- Source dataset
- uspto-grants-1987_03
- Patent number
- US04647694
Reaction notes
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