Aniline → HCID 70551414, compound

HRID 2049107Notes

Reaction equation

HRID 2049107 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]1(=[O:14])[O:13][C:11](=O)[CH:10]=[CH:9]1.[C:15]1([N:21]=[C:22]=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN1CCCC1=O>[C:2]1([N:1]2[CH:10]([CH2:9][C:8]([NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:14])[C:11](=[O:13])[N:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:22]2=[O:23])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 7672Phenyl isocyanateHCID 7923Maleic Anhydride

Product 1

HCID 70551414HCID 70551414, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

93 g of aniline are added dropwise with cooling at approximately 30° C. to a solution of 98 g of maleic acid anhydride in 300 g of N-methyl pyrrolidone. To complete the formation of the amido acid, the mixture is then stirred for 1 hour at the above-mentioned temperature. 238 g of phenyl isocyanate are then added dropwise at 20° C. and the condensation reaction is carried out with stirring for 1 hour at 50° C., for 2 hours at 90° C., for 2 hours at 120° C. and for 6 hours at 150° C. The reaction product crystallises out on cooling and is recrystallised from acetonitrile and from metahnol. 1,3-Diphenyl-5-(N-phenylaminocarbonylmethyl)-hydantoin is obtained in the form of colourless crystals melting at 214° to 215° C.

Workup

  1. customthe condensation reaction
  2. stirringwith stirring for 1 hour at 50° C., for 2 hours at 90° C., for 2 hours at 120° C. and for 6 hours at 150° C
  3. customThe reaction product crystallises out
  4. temperatureon cooling
  5. customis recrystallised from acetonitrile and from metahnol

Sources & evidence

ORD record
ord-b71dee722dcd4da794407142600e38de
Source dataset
uspto-grants-1980_04
Patent number
US04196274

Reaction notes

Loading…