Triethylamine → HCID 15070158, compound

HRID 1073019Notes

Reaction equation

HRID 1073019 reaction equation
[Cl:1][C:2]1[C:3]([O:12][C:13]2[CH:24]=[CH:23][C:16]([O:17][CH:18]([CH3:22])[C:19](Cl)=[O:20])=[CH:15][CH:14]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.Cl.[NH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=1.C(N(CC)CC)C>C(#N)C>[Cl:1][C:2]1[C:3]([O:12][C:13]2[CH:24]=[CH:23][C:16]([O:17][CH:18]([CH3:22])[C:19]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:34])([F:35])[F:36])=[CH:29][CH:28]=3)=[O:20])=[CH:15][CH:14]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27239614-(Trifluoromethyl)anilinium chlorideHCID 13389070HCID 13389070, compound

Product 1

HCID 15070158HCID 15070158, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of the 2-(4-((3-chloro-5-(trifluoromethyl)-2-pyridinyl)oxy)phenoxy)propionyl chloride (prepared in Step A) in 50 ml of acetonitrile was added to a mixture of 3.82 g (19.4 mmol) of 4-aminobenzotrifluoride, hydrochloride and 4.90 g (48.4 mmol) of triethylamine in 25 ml of acetonitrile. The reaction mixture was warmed at reflux for 4.0 hours and then poured over crushed ice. The resulting precipitate was collected by filtration and dried. The residual solid was recrystallized from methylcyclohexane to give 9.1 g (93 percent of theoretical) of the above-named product as a tan solid which melted at 140°-143° C. The structure of the product was confirmed by its IR and NMR spectrum. (Compound 1)

Workup

  1. temperatureThe reaction mixture was warmed
  2. temperatureat reflux for 4.0 hours
  3. additionpoured
  4. customover crushed ice
  5. filtrationThe resulting precipitate was collected by filtration
  6. customdried
  7. customThe residual solid was recrystallized from methylcyclohexane

Sources & evidence

ORD record
ord-b29a166c5946459a88b3e8dfa6243f90
Source dataset
uspto-grants-1990_11
Patent number
US04968343

Reaction notes

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