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Water → N-(4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl)-4-chloronicotinamide

HRID 1867653
Notes
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Reaction equation

HRID 1867653 reaction equation
[Cl:1][C:2]1[C:3]([O:12][C:13]2[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C(N(CC)CC)C.Cl.[Cl:28][C:29]1[C:34]([C:35](Cl)=[O:36])=[CH:33][N:32]=[CH:31][CH:30]=1.O>O1CCCC1>[Cl:1][C:2]1[C:3]([O:12][C:13]2[CH:19]=[CH:18][C:16]([NH:17][C:35](=[O:36])[C:34]3[C:29]([Cl:28])=[CH:30][CH:31]=[N:32][CH:33]=3)=[CH:15][CH:14]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27641164-{[3-Chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}anilineHCID 231520084-Chloronicotinoyl chloride hydrochloride

Product 1

HCID 23151884N-(4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl)-4-chloronicotinamide

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

A solution of 150 mg of 4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)aniline and 116 mg of triethylamine in 5 mL of tetrahydrofuran was stirred with 100 mg of 4-chloronicotinoyl chloride hydrochloride for about 50 minutes, and after addition of water, the precipitated crystals were recovered by filtration. The recovered crystals were washed with ether and dried to 106 mg of N-(4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl)-4-chloronicotinamide having a melting point of 178-180° C. (decomposition).

Workup

  1. filtrationthe precipitated crystals were recovered by filtration
  2. washThe recovered crystals were washed with ether
  3. dry with materialdried to 106 mg of N-(4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl)-4-chloronicotinamide having a melting point of 178-180° C. (decomposition)

Sources & evidence

ORD record
ord-afe8394e47b649088fd1799f755c126a
Source dataset
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07632865B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes