1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → N-(4-(6-Chloropyrimidin-4yl-oxy)phenyl)-N'-(4-chloro-3-trifluoromethyl-phenyl)-urea

HRID 1993514Notes

Reaction equation

HRID 1993514 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)[CH:3]=1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]=[O:25])=[CH:19][C:18]=1[C:26]([F:29])([F:28])[F:27]>C1COCC1.CCOC(C)=O.C([O-])(O)=O.[Na+].O>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:15]=[CH:14][C:12]([NH:13][C:24]([NH:23][C:20]3[CH:21]=[CH:22][C:17]([Cl:16])=[C:18]([C:26]([F:28])([F:27])[F:29])[CH:19]=3)=[O:25])=[CH:11][CH:10]=2)[CH:3]=1

Participants

7

Reactant 2

HCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 226137114-((6-Chloropyrimidin-4-yl)oxy)aniline

Product 1

HCID 58659336N-(4-(6-Chloropyrimidin-4yl-oxy)phenyl)-N'-(4-chloro-3-trifluoromethyl-phenyl)-urea

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 4-(6-chloro-pyrimidin-4-yl-oxy)-aniline (Stage 21.1; 3.77 g, 15 mmol) in THF (40 ml) under N2-atmosphere, 4-chloro-3-trifluoromethylphenyl isocyanate (4.98 g, 22.5 mmol) dissolved in THF (20 ml) is added. After 1 h at rt the solution is diluted with AcOEt and NaHCO3 in water, the aqueous layer separated off and extracted twice with AcOEt. The organic phases are washed with water and brine, dried (Na2SO4) and concentrated in vacuo. Stirring of the resulting solid in Et2O finally yields the title compound: m.p.: 180-181° C.; 1H-NMR (DMSO-d6): 9.22 (s, HN), 8.97 (s, HN), 8.65 (s, 1H), 8.11 (s, 1H), 7.65 (m, 1H), 7.63 (m, 1H), 7.53 (d, 2H), 7.34 (s, 1H), 7.19 (d, 2H); Anal.: CHNClFO.

Workup

  1. additionis added
  2. customthe aqueous layer separated off
  3. extractionextracted twice with AcOEt
  4. washThe organic phases are washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-739766ac591242cb802cf0e1c2f2f10e
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

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