3-Chloro-4-fluoroaniline → 3-(3-Chloro-4-fluorophenyl)-5-methyl-hydantoin

HRID 224947Notes

Reaction equation

HRID 224947 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].C([O:12][C:13](=O)[CH:14]([N:16]=[C:17]=[O:18])[CH3:15])C>>[Cl:1][C:2]1[CH:3]=[C:4]([N:5]2[C:13](=[O:12])[CH:14]([CH3:15])[NH:16][C:17]2=[O:18])[CH:6]=[CH:7][C:8]=1[F:9]

Participants

3

Reactant 2

HCID 97083-Chloro-4-fluoroanilineHCID 550681Ethyl 2-isocyanatopropionate

Product 1

HCID 233308883-(3-Chloro-4-fluorophenyl)-5-methyl-hydantoin

Procedure

A mixture of 2.91 g (20 mmol) of 3-chloro-4-fluoroaniline and 3.01 g (21 mmol) of 2-isocyanato-propionic acid ethyl ester was maintained at 130°-140° C. for 91/2 hours. The resulting product was crystallized from chloroform/methanol to yield 3-(3-chloro-4-fluorophenyl)-5-methyl-hydantoin, m.p. 174°-175.5° C.

Workup

  1. temperaturewas maintained at 130°-140° C. for 91/2 hours
  2. customThe resulting product was crystallized from chloroform/methanol

Sources & evidence

ORD record
ord-b7faf9d5b1ea471a9164a5baa35d0a30
Source dataset
uspto-grants-1980_11
Patent number
US04234736

Reaction notes

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