O-Cresol → 1,3-Dimethyl-5-(phenylaminocarbonyl methylene)-hydantoin

HRID 263097

Reaction equation

HRID 263097 reaction equation
[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]

Participants

4

Reactant 3

HCID 335O-CresolHCID 7293N,N'-DimethylureaHCID 1550938Maleic acid anilide

Product 1

HCID 540892721,3-Dimethyl-5-(phenylaminocarbonyl methylene)-hydantoin

Conditions

Temperature
165 °C

Procedure

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.

Workup

  1. distillationThe solvent is distilled off in vacuo
  2. distillationAn oily liquid distills over at a boiling point of from 220° to 223° C./0.1 Torr
  3. customRecrystallisation from n-propanol
  4. customgives the compound

Sources & evidence

ORD record
ord-0aac9f2dd7fc4702b97da29a8053b702
Source dataset
uspto-grants-1979_05
Patent number
US04156074

Linked notes

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