O-Cresol → 1,3-Dimethyl-5-(phenylaminocarbonyl methylene)-hydantoin
Reaktionsgleichung
[C:1]1([NH:7][C:8](=[O:14])/[CH:9]=[CH:10]\[C:11]([OH:13])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15][NH:16][C:17]([NH:19][CH3:20])=[O:18].C1(C)C(O)=CC=CC=1>>[CH3:15][N:16]1[C:10](=[CH:9][C:8]([NH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:14])[C:11](=[O:13])[N:19]([CH3:20])[C:17]1=[O:18]Komponenten
4
Reaktionsbedingungen
- Temperatur
- 165 °C
Versuchsvorschrift
A mixture of 19.1 parts of N-phenyl maleic acid monoamide 8.8 parts of N,N'-dimethyl urea and 100 parts of cresol is stirred for 2.5 hours at 165° C. The solvent is distilled off in vacuo and the residue fractionated. An oily liquid distills over at a boiling point of from 220° to 223° C./0.1 Torr and solidifies after a while. Recrystallisation from n-propanol gives the compound confirmed by IR- (bands characteristic of hydantoins at 1705 and 1765 cm-1 and of amide at 1690 cm-1) and NMR-spectra.