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

HRID 1010826Notes

Reaction equation

HRID 1010826 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 the reaction mixture on an ice bath. The mixture reaction was stirred overnight at room temperature. Most of the pyridine was removed and 100 ml of cold water was added to precipitate the product. The product was isolated by filtration, washed with cold water and a small amount of cold ethanol, and dried under vacuum to obtain 9.15 g of product (yield: 50%).

Workup

  1. temperaturewhile cooling the reaction mixture on an ice bath
  2. customThe mixture reaction
  3. customMost of the pyridine was removed
  4. addition100 ml of cold water was added
  5. customto precipitate the product
  6. customThe product was isolated by filtration
  7. washwashed with cold water
  8. dry with materiala small amount of cold ethanol, and dried under vacuum

Sources & evidence

ORD record
ord-d5c8c7c4799f47b9859592528f0666bc
Source dataset
uspto-grants-2011_07
Patent number
US07977342B2

Reaction notes

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