1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → HCID 23154980, compound

HRID 1912755Notes

Reaction equation

HRID 1912755 reaction equation
[N:1]1([C:10]2[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=2)[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[N:3]=[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:1]3[C:9]4[CH:8]=[CH:7][N:6]=[CH:5][C:4]=4[N:3]=[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 23155220HCID 23155220, compound

Product 1

HCID 23154980HCID 23154980, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 4-(imidazo[4,5-c]pyridin-1-yl)aniline prepared in Step B was dissolved in 10 mL of dichloromethane, and 30 mg (0.137 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 reduce pressure, and the obtained crude product was recrystallized from ethyl acetate to obtain 35.0 mg (51%) of 1-(4-chloro-3-(trifluoromethyl)-phenyl)-3-(4-imidazo[4,5-c]pyridin-1-ylphenyl)urea (Table 1, Compound No. 1) as a colorless crystal.

Workup

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

Sources & evidence

ORD record
ord-b51c77af2c7d456285818d97d870f509
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

Loading…