Aniline → HCID 54452345, compound

HRID 426649Notes

Reaction equation

HRID 426649 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]1([N:14]2[C:18](=[O:19])[CH:17]=[CH:16][C:15]2=[O:20])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:21]1([N:27]=[C:28]=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[N:30]12CCN(CC1)CC2.N1CC(=O)NC1=O>ClC1C=CC=CC=1Cl>[C:21]1([N:27]2[C:17](=[C:16]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:15]([NH2:30])=[O:20])[C:18](=[O:19])[N:14]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:28]2=[O:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 5

HCID 6115AnilineHCID 7672Phenyl isocyanateHCID 9237DabcoHCID 10006HydantoinHCID 13662N-Phenylmaleimide

Product 1

HCID 54452345HCID 54452345, compound

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
175 °C

Procedure

26.6 parts of the compound ##STR5## (from aniline and N-phenyl maleic imide) are dissolved in 100 ml of o-dichlorobenzene. 11.9 parts of phenylisocyanate are added and the reaction mixture is left to stand overnight. After the addition of 0.1 g of 1,4-diaza-bicyclo-[2,2,2]-octane, the solution is stirred for 6 hours at 175° C., the solvent is distilled off under vacuum and toluene is added to the residue. The crystalline precipitate obtained is suction filtered and recrystallised from ethyl acetate. The structure obtained by calculation is confirmed by the NMR- and IR-spectra (for hydantoin 1715 and 1770 cm-1 ; for amide 1690 cm-1).

Workup

  1. waitthe reaction mixture is left
  2. distillationthe solvent is distilled off under vacuum and toluene
  3. additionis added to the residue
  4. customThe crystalline precipitate obtained
  5. filtrationfiltered
  6. customrecrystallised from ethyl acetate
  7. customThe structure obtained by calculation

Sources & evidence

ORD record
ord-e5e0af98372b4a34ac73984ae3dbad52
Source dataset
uspto-grants-1979_10
Patent number
US04170701

Reaction notes

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