1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → HCID 23155264, compound

HRID 1912788Notes

Reaction equation

HRID 1912788 reaction equation
[N:1]1([C:10]2[CH:15]=[CH:14][C:13]([NH:16][OH:17])=[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:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:26]=[O:27])=[CH:21][C:20]=1[C:28]([F:31])([F:30])[F:29]>C(Cl)Cl>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([N:16]([OH:17])[C:13]2[CH:12]=[CH:11][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:15][CH:14]=2)=[O:27])=[CH:21][C:20]=1[C:28]([F:29])([F:30])[F:31]

Participants

4

Reactant 2

HCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 23155121HCID 23155121, compound

Product 1

HCID 23155264HCID 23155264, compoundYield 16.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 5 mL of methylene chloride, 37 mg of N-(4-imidazo[4,5-c]pyridin-1-yl-phenyl)hydroxylamine obtained in Step A was dissolved, and 41 mg (1.84 mmol) of 4-chloro-3-(trifluoromethyl)phenyl isocyanate was added thereto and the mixture solution was stirred at room temperature for three hours. The reaction solution was concentrated, and then the residue was partitioned between ethyl acetate and a saturated ammonium chloride aqueous solution. The organic layer was washed with a saturated sodium chloride solution, dried and concentrated under reduced pressure. The residue was triturated with n-hexane:ethyl acetate=1:1 to obtain 12 mg (16%) of 1-(4-chloro-3-(trifluoromethyl)phenyl)-3-hydroxy-3-(4-imidazo-[4,5-c]pyridin-1-ylphenyl)urea (Table 1, Compound No. 45) as a white solid.

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe residue was partitioned between ethyl acetate
  3. washThe organic layer was washed with a saturated sodium chloride solution
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was triturated with n-hexane

Sources & evidence

ORD record
ord-c9971faf3b644b118e3fdc9040130bd5
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

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