2-Fluorobenzoyl chloride → N-(4-Cyano-1,3-dimethyl-1H-pyrazol-5-yl)-2-fluorobenzamide

HRID 1354295Notes

Reaction equation

HRID 1354295 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[C:9]#[N:10].[F:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14](Cl)=[O:15]>N1C=CC=CC=1>[C:9]([C:3]1[C:4]([CH3:8])=[N:5][N:6]([CH3:7])[C:2]=1[NH:1][C:14](=[O:15])[C:13]1[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=1[F:11])#[N:10]

Participants

4

Reactant 2

HCID 98082-Fluorobenzoyl chlorideHCID 2198705-amino-1,3-dimethyl-1H-pyrazole-4-carbonitrile

Product 1

HCID 17088883N-(4-Cyano-1,3-dimethyl-1H-pyrazol-5-yl)-2-fluorobenzamideYield 50%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Amino-1,3-dimethyl-1H-pyrazole-4-carbonitrile (10 g, 73.4 mmole) was suspended in pyridine (90 ml) and 2-fluorobenzoyl chloride was added dropwise while cooling reaction mixture on an ice bath. Stirred reaction mixture overnight at room temperature. Removed most of the pyridine and added 100 ml cold water to precipitate the product. Isolated product by filtration, washed with cold water, small amount of cold ethanol and dried under vacuum to obtain 9.15 g product (yield: 50%).

Workup

  1. temperaturewhile cooling
  2. customreaction mixture on an ice bath
  3. customreaction mixture overnight at room temperature
  4. customRemoved most of the pyridine
  5. additionadded 100 ml cold water
  6. customto precipitate the product
  7. filtrationIsolated product by filtration
  8. washwashed with cold water, small amount of cold ethanol
  9. customdried under vacuum

Sources & evidence

ORD record
ord-d2f4b17e7a6d4c1b8ac44150bdc5681c
Source dataset
uspto-grants-2007_05
Patent number
US07223766B2

Reaction notes

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