Triethylamine → HCID 15070166, compound

HRID 1073021Notes

Reaction equation

HRID 1073021 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][C:13]1[CH:24]=[CH:23][C:16]([O:17][CH:18]([CH3:22])[C:19](Cl)=[O:20])=[CH:15][CH:14]=1)[CH:6]=[N:5]2.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[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][C:13]1[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]=1)[CH:6]=[N:5]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27239614-(Trifluoromethyl)anilinium chlorideHCID 133700182-(4-((6-Chloro-2-quinoxalinyl)oxy)phenoxy)propanoyl chloride

Product 1

HCID 15070166HCID 15070166, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 7.25 mmol of 2-(4-((6-chloro-2-quinoxalinyl)oxy)phenoxy)propionyl chloride, prepared using substantially the procedure of Step A of Example 1 from the corresponding acid, in 20 ml of acetonitrile was added to solution of 1.43 g (7.25 mmol) of 4-aminobenzotrifluoride, hydrochloride and 1.83 g (18.1 mmol) of triethylamine in 10 ml of acetonitrile. The reaction mixture was warmed at reflux for a period of 4 hours and then poured over crushed ice. The resulting precipitate was collected by filtration and then recrystallized from acetonitrile to give 2.40 g (68 percent of theoretical) of the above-named product as a tan solid which melted at 176°-178° C. The structure of the product was confirmed by its IR and NMR spectrum. (Compound 5)

Workup

  1. temperatureThe reaction mixture was warmed
  2. temperatureat reflux for a period of 4 hours
  3. additionpoured
  4. customover crushed ice
  5. filtrationThe resulting precipitate was collected by filtration
  6. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-2c9e7a373d2d492894c8e89dd98de2f0
Source dataset
uspto-grants-1990_11
Patent number
US04968343

Reaction notes

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