Triethylamine → HCID 11428847, compound

HRID 1391430Notes

Reaction equation

HRID 1391430 reaction equation
[Cl:1][C:2]1[C:3]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.C(Cl)(=O)C(Cl)=O.[F:23][C:24]([F:33])([F:32])[C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1.C(N(CC)CC)C.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[C:3]([C:8]2[CH:9]=[CH:10][C:11]([C:12]([NH:29][C:28]3[CH:30]=[CH:31][C:25]([C:24]([F:23])([F:32])[F:33])=[CH:26][CH:27]=3)=[O:14])=[CH:15][CH:16]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 99644-(Trifluoromethyl)anilineHCID 10340Sodium CarbonateHCID 65578Oxalyl chlorideHCID 221704544-(3-Chloropyridin-2-yl)benzoic acid

Product 1

HCID 11428847HCID 11428847, compoundYield 49.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-(3-chloro-pyridin-2-yl)-benzoic acid (5.0 g, 21.4 mmol) in methylene chloride (100 mL) at ambient temperature was added oxalyl chloride (5.43 g, 42.79 mmol) followed by two drops of DMF and the mixture was heated to reflux for 30 minutes. The clear solution was then concentrated to dryness, dissolved in methylene chloride (100 mL) and was treated with 4-trifluoromethyl aniline (4.14 g, 25.68 mmol) followed by triethylamine (2.6 g, 25.68 mmol) and the mixture was gently heated to reflux for 30 minutes and agitated overnight at ambient temperature. After treating the mixture with sat. Na2CO3, the organic layer was separated, washed with water, dried and concentrated to give the crude product which was chromatographed on silicagel to obtain 4.0 g (49.6%) of the title compound as a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 30 minutes
  3. concentrationThe clear solution was then concentrated to dryness
  4. dissolutiondissolved in methylene chloride (100 mL)
  5. temperaturethe mixture was gently heated
  6. temperatureto reflux for 30 minutes
  7. customthe organic layer was separated
  8. washwashed with water
  9. customdried
  10. concentrationconcentrated
  11. customto give the crude product which
  12. customwas chromatographed on silicagel

Sources & evidence

ORD record
ord-61bbe4a32cd14061886023ac69d71603
Source dataset
uspto-grants-2008_03
Patent number
US07338950B2

Reaction notes

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