3-Amino-5-fluorobenzonitrile → 1-(2-Chloro-4-trifluoromethylphenyl)-3-(3-cyano-5-fluorophenyl)urea

HRID 384233Notes

Reaction equation

HRID 384233 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]#[N:10])[CH:5]=[C:6]([CH:8]=1)[NH2:7].[Cl:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=1[N:22]=[C:23]=[O:24]>O1CCCC1>[Cl:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=1[NH:22][C:23]([NH:7][C:6]1[CH:8]=[C:2]([F:1])[CH:3]=[C:4]([C:9]#[N:10])[CH:5]=1)=[O:24]

Participants

4

Reactant 2

HCID 27564323-Amino-5-fluorobenzonitrileHCID 51025332-Chloro-4-(trifluoromethyl)phenyl isocyanate

Product 1

HCID 668987601-(2-Chloro-4-trifluoromethylphenyl)-3-(3-cyano-5-fluorophenyl)ureaYield 84.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 15 g (110.2 mmol) of 5-fluoro-3-cyanoaniline in 150 ml of tetrahydrofuran is stirred at ambient temperature under an argon atmosphere. Next, 17.5 ml (121.22 mmol) of 2-chloro-4-trifluoromethylphenylisocyanate are added. The reaction medium is heated at reflux for 3 hours then concentrated to dryness using a rotary evaporator. The solid residue obtained is recrystallized at high temperature in 60 ml of ethyl acetate in order to give 33.25 g of 1-(2-chloro-4-trifluoromethylphenyl)-3-(3-cyano-5-fluorophenyl)urea in the form of a white solid.

Workup

  1. temperatureThe reaction medium is heated
  2. temperatureat reflux for 3 hours
  3. concentrationthen concentrated to dryness
  4. customa rotary evaporator
  5. customThe solid residue obtained
  6. customis recrystallized at high temperature in 60 ml of ethyl acetate in order

Sources & evidence

ORD record
ord-994db13d8f6741d181374bec16f2100a
Source dataset
uspto-grants-2013_02
Patent number
US08367715B2

Reaction notes

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