Triethylamine → N-(3-chloro-4-(3-chlorophenoxy)phenyl)picolinamide

HRID 38243

Reaction equation

HRID 38243 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](Cl)=[O:9].CCN(CC)CC.[Cl:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][C:25]=1[O:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=1)[NH2:22]>C(Cl)Cl>[Cl:18][C:19]1[CH:20]=[C:21]([NH:22][C:8](=[O:9])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=2)[CH:23]=[CH:24][C:25]=1[O:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 135033Picolinoyl Chloride HydrochlorideHCID 176055343-Chloro-4-(3-chlorophenoxy)aniline

Product 1

HCID 42645239N-(3-chloro-4-(3-chlorophenoxy)phenyl)picolinamideYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to Scheme 3 Step 3: Picolinoyl chloride hydrochloride (1.52 mmol, 271 mg) and Et3N (3.05 mmol, 0.42 mL) were added sequentially to a solution of 3-chloro-4-(3-chlorophenoxy)aniline (1.02 mmol, 258 mg) in DCM (6 mL) at 0° C. The reaction mixture was stirred at room temperature for 2 hours. The organic phase was washed with a saturated solution of NaHCO3 and with brine, was dried over MgSO4, was filtered and was concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel using cyclohexane/AcOEt (90:10) as eluent to afford N-(3-chloro-4-(3-chlorophenoxy)phenyl)picolinamide (0.52 mmol, 187 mg, 51%) as a white solid.

Workup

  1. washThe organic phase was washed with a saturated solution of NaHCO3 and with brine
  2. dry with materialwas dried over MgSO4
  3. filtrationwas filtered
  4. concentrationwas concentrated under reduced pressure
  5. customThe crude product was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-4dd49d5ee1784637a7cfe86cc55f2823
Source dataset
uspto-grants-2013_09
Patent number
US08524726B2

Linked notes

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