Dimethylformamide → HCID 56949532, compound

HRID 1641465Notes

Reaction equation

HRID 1641465 reaction equation
[Br:1][C:2]1[CH:6]=[C:5]([C:7](O)=[O:8])[N:4]([C:10]2[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][N:11]=2)[N:3]=1.S(Cl)([Cl:19])=O.CN(C=O)C>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:6]=[C:5]([C:7]([Cl:19])=[O:8])[N:4]([C:10]2[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][N:11]=2)[N:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 115875353-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid

Product 1

HCID 56949532HCID 56949532, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.52 g of 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid was dissolved in 10 ml of chloroform, 0.55 ml of thionyl chloride was dropwise added, and 0.05 ml of DMF was added, followed by reflux for 30 minutes. After the reaction liquid was stood to cool, the solvent was distilled off under reduced pressure to obtain crude product of 3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyl chloride. Then, a mixed solution comprising the above crude product and 5 ml of toluene was dropwise added to a mixed solution comprising 0.5 ml of ethanethiol, 1.11 ml of triethylamine and 20 ml of chloroform under cooling with ice, followed by stirring for 5 minutes and reaction at room temperature for 14 hours. The reaction solvent was distilled off under reduced pressure, and 50 ml of water was added, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/0 to 3/1) to obtain 1.4 g of the desired product in the form of light red crystals (melting point: 94° C.).

Workup

  1. temperatureby reflux for 30 minutes
  2. customAfter the reaction liquid
  3. temperatureto cool
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9183c00f6ce64bf0a4a1a48bbcc550e6
Source dataset
uspto-grants-2012_02
Patent number
US08115006B2

Reaction notes

Loading…