2-(Trifluoromethyl)benzoyl chloride → HCID 44203150, compound

HRID 1715680Notes

Reaction equation

HRID 1715680 reaction equation
[NH2:1][C:2]1[C:3]([Cl:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[F:9][C:10]([F:21])([F:20])[C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13](Cl)=[O:14]>N1C=CC=CC=1>[Cl:8][C:3]1[C:2]([NH:1][C:13](=[O:14])[C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[C:10]([F:9])([F:20])[F:21])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 805282-Chloro-3-pyridylamine

Product 1

HCID 44203150HCID 44203150, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4.57 g 3-amino-2-chloropyridine (36 mmol) and 30 mL pyridine were mixed in an ice bath. 8.24 g 2-trifluoromethyl benzoyl chloride (40 mol) was then added. After return to room temperature and reaction for 4 hr, the reaction was quenched by water. After extraction three times by ethyl acetate, an ethyl acetate layer was collected and washed by 1M HCl solution. After drying, filtration, concentration, and purification by silicon-gel column, 9.9 g solid was obtained, with a yield of 92%.

Workup

  1. customAfter return to room temperature and reaction for 4 hr
  2. customthe reaction was quenched by water
  3. extractionAfter extraction three times by ethyl acetate
  4. customan ethyl acetate layer was collected
  5. washwashed by 1M HCl solution
  6. customAfter drying
  7. filtrationfiltration, concentration, and purification by silicon-gel column

Sources & evidence

ORD record
ord-3fe655a851dd4986a40ebd37654f7967
Source dataset
uspto-grants-2010_09
Patent number
US07799918B2

Reaction notes

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