1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → HCID 23155191, compound

HRID 1912756Notes

Reaction equation

HRID 1912756 reaction equation
[N:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[N:3]([C:10]2[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=2)[CH:2]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]=[C:25]=[O:26])=[CH:20][C:19]=1[C:27]([F:30])([F:29])[F:28]>ClCCl>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:14][C:13]2[CH:15]=[CH:16][C:10]([N:3]3[C:4]4[CH:5]=[N:6][CH:7]=[CH:8][C:9]=4[N:1]=[CH:2]3)=[CH:11][CH:12]=2)=[O:26])=[CH:20][C:19]=1[C:27]([F:28])([F:29])[F:30]

Participants

4

Reactant 2

HCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 23155248HCID 23155248, compound

Product 1

HCID 23155191HCID 23155191, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 4-(imidazo[4,5-c]pyridin-3-yl)aniline prepared in Step A was dissolved in 10 mL of dichloromethane, and 14.2 mg (0.064 mmol) of 4-chloro-3-(trifluoromethyl)phenyl isocyanate was added thereto and the mixture solution was stirred at room temperature for three hours. The solvent was distilled under reduced pressure, and the obtained crude product was recrystallized from ethyl acetate to obtain 20.2 mg (73%) of 1-(4-chloro-3-(trifluoromethyl)-phenyl)-3-(4-imidazo[4,5-c]pyridin-3-ylphenyl)urea (Table 1, Compound No. 2) as a colorless crystal.

Workup

  1. distillationThe solvent was distilled under reduced pressure
  2. customthe obtained crude product
  3. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-219114829c6543118acf6a58dbe5a285
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

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