2-Fluorobenzoyl chloride → HCID 21104353, compound

HRID 1010830Notes

Reaction equation

HRID 1010830 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>[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

4

Reactant 2

HCID 98082-Fluorobenzoyl chlorideHCID 21104345HCID 21104345, compound

Product 1

HCID 21104353HCID 21104353, compoundYield 24.7%

Reagents, catalysts & solvents 1

HCID 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 the reaction mixture was stirred for 1 hour at 0° C., and at room temperature overnight. The solvent was removed under vacuum. The residue was taken up in ethyl acetate, washed with diluted hydrochloric acid, 0.1 M sodium hydroxide, and water, and dried over sodium sulfate (anh). The solvent was removed and the solid triturated in 30% ethyl acetate/hexanes. The product was filtered to obtain 4.16 g product (yield: 24%).

Workup

  1. customat room temperature
  2. customovernight
  3. customThe solvent was removed under vacuum
  4. washwashed with diluted hydrochloric acid, 0.1 M sodium hydroxide, and water
  5. dry with materialdried over sodium sulfate (anh)
  6. customThe solvent was removed
  7. customthe solid triturated in 30% ethyl acetate/hexanes
  8. filtrationThe product was filtered

Sources & evidence

ORD record
ord-05cc253cd82a476ea14a1ccde5a0cfb0
Source dataset
uspto-grants-2011_07
Patent number
US07977342B2

Reaction notes

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