Thionyl Chloride → HCID 53679607, compound

HRID 1614495Notes

Reaction equation

HRID 1614495 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][N:6]([C:13]2[C:18]([Cl:19])=[CH:17][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][N:14]=2)[C:7]=1[CH:8]=[CH:9][C:10](O)=[O:11])#[N:2].S(Cl)([Cl:26])=O>C1(C)C=CC=CC=1>[C:1]([C:3]1[CH:4]=[N:5][N:6]([C:13]2[C:18]([Cl:19])=[CH:17][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][N:14]=2)[C:7]=1[CH:8]=[CH:9][C:10]([Cl:26])=[O:11])#[N:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 54321359HCID 54321359, compound

Product 1

HCID 53679607HCID 53679607, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
98 °C

Procedure

A stirred slurry of 1.1 grams (0.003 mole) of 3-[4-cyano-1-(3-chloro-5-trifluoromethylpyridin-2-yl)-1H-pyrazol-5-yl]acrylic acid and 1.0 mL of thionyl chloride in 20 mL of toluene was heated at about 72° C. for 25 minutes. The slurry was warmed to 98° C. over a 45 minutes period, during which time the reaction mixture became homogeneous. The reaction mixture was heated at 98° C. for 35 minutes. After this time, the reaction mixture was cooled and concentrated under reduced pressure, yielding 1.1 grams of 3-[4-cyano-1-(3-chloro-5-trifluoromethylpyridin-2-yl)-1H-pyrazol-5-yl]acrylic acid chloride. The acid chloride was used without purification.

Workup

  1. temperatureThe reaction mixture was heated at 98° C. for 35 minutes
  2. temperatureAfter this time, the reaction mixture was cooled
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e1e5f29d5c8f45d9941d6c20897148d2
Source dataset
uspto-grants-1993_03
Patent number
US05198014

Reaction notes

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