Dichloromethane → HCID 694776, compound

HRID 2099115Notes

Reaction equation

HRID 2099115 reaction equation
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.ClCCl.[F:21][C:22]([F:31])([F:30])[C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][CH:29]=1)[NH2:26]>O>[F:21][C:22]([F:30])([F:31])[C:23]1[CH:24]=[C:25]([NH:26][C:2](=[O:9])[C:3]2[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=2)[CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 73753-(Trifluoromethyl)anilineHCID 8471TriethylamineHCID 12262826Isonicotinoyl chloride hydrochloride

Product 1

HCID 694776HCID 694776, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Isonicotinoyl chloride hydrochloride (670 mg, 3.76 mmol, commercially available product) and triethylamine (864 μl, 6.20 mmol) were sequentially added at 0° C. to a dichloromethane (5 ml) solution of 3-(trifluoromethyl)aniline (208 mg, 1.29 mmol, commercially available product). The resulting mixture was warmed to room temperature and stirred for 23 hours. Water was added to the mixture, and the resulting mixture was extracted three times with ethyl acetate. The obtained organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by recrystallization (ethyl acetate). Thus, N-[3-(trifluoromethyl)phenyl]isonicotinamide (GIF-0608) (166 mg, 48.3%) was yielded as a colorless solid.

Workup

  1. extractionthe resulting mixture was extracted three times with ethyl acetate
  2. washThe obtained organic layer was washed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by recrystallization (ethyl acetate)

Sources & evidence

ORD record
ord-68e565f3b6674bf6bfff69604b85c531
Source dataset
uspto-grants-2009_08
Patent number
US07569536B2

Reaction notes

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