2-Fluorobenzoyl chloride → HCID 21104353, compound

HRID 1354299Notes

Reaction equation

HRID 1354299 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][CH2:8][CH2:9][CH3:10])[N:5]=[C:4]([CH3:11])[C:3]=1[C:12]#[N:13].[F:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17](Cl)=[O:18]>ClCCl.N1C=CC=CC=1.C(OCC)(=O)C>[CH2:7]([N:6]1[C:2]([NH:1][C:17](=[O:18])[C:16]2[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=2[F:14])=[C:3]([C:12]#[N:13])[C:4]([CH3:11])=[N:5]1)[CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 2

HCID 98082-Fluorobenzoyl chlorideHCID 21104345HCID 21104345, compound

Product 1

HCID 21104353HCID 21104353, compoundYield 24.7%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21875418Pyridine methylene chlorideSolvent

Conditions

Temperature
0 °C

Procedure

5-Amino-1-butyl-3-methyl-1H-pyrazole-4-carbonitrile (10.0 g, 56 mmole) was dissolved in a mixture of dichloromethane/pyridine (45 ml/15 ml) and cooled to 0° C. 2-fluorobenzoyl chloride (8.87 g, 56 mmole) was added dropwise and reaction mixture stirred for 1 hour at 0° C., the at room temperature overnight. Removed solvent under vacuum. Residue was taken up in ethyl acetate, washed with dilute hydrochloric acid, 0.1M sodium hydroxide, water and dried over sodium sulfate (anh). Removed solvent and triturated solid in 30% ethyl acetate/hexanes. Filtered product to obtain 4.16 g product (yield: 24%).

Workup

  1. customreaction mixture
  2. customat room temperature
  3. customovernight
  4. washwashed with dilute hydrochloric acid, 0.1M sodium hydroxide, water
  5. dry with materialdried over sodium sulfate (anh)
  6. customRemoved solvent and triturated solid in 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-0fd213290ba74bb2afb4bcb97ffb7067
Source dataset
uspto-grants-2007_05
Patent number
US07223766B2

Reaction notes

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