Thionyl Chloride → HCID 54495530, compound

HRID 1109444Notes

Reaction equation

HRID 1109444 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([C:18]([OH:20])=O)=[C:16]([C:21]#[N:22])[CH:15]=[N:14]1.S(Cl)([Cl:25])=O>>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:11])[F:10])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([C:18]([Cl:25])=[O:20])=[C:16]([C:21]#[N:22])[CH:15]=[N:14]1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 13823574HCID 13823574, compound

Product 1

HCID 54495530HCID 54495530, compoundYield 58.5%

Procedure

A slurry of 12.0 g (0.0343 mole) of 1-(2,6-dichloro-4-trifluoromethylphenyl)-4-cyano-1H-5-pyrazolylcarboxylic acid in 30 mL (49 g, 0.41 mole) of thionyl chloride was heated at gentle reflux for approximately 62 hours, after which it had become a dark solution. This solution was cooled, and the excess thionyl chloride was evaporated under reduced pressure, leaving a residue. Petroleum ether was added to this residue, causing a precipitate, which, upon filtration, yielded 7.4 g of 1-(2,6-dichloro-4-trifluoromethylphenyl)-4-cyano-1H-5-pyrazolylcarboxylic acid chloride as a solid, mp 100°-102° C. The NMR spectrum was consistent with the proposed structure. A second crop of tacky crystals was obtained by chilling the filtrate obtained when the product was isolated by filtration. The NMR spectrum of the second crop of crystals was consistent with the proposed structure, but showed also that it was contaminated with some starting material.

Workup

  1. temperatureat gentle reflux for approximately 62 hours
  2. temperatureThis solution was cooled
  3. customthe excess thionyl chloride was evaporated under reduced pressure
  4. customleaving a residue
  5. filtrationupon filtration

Sources & evidence

ORD record
ord-11fe8ca67f21416cb22111631c9a572b
Source dataset
uspto-grants-1994_06
Patent number
US05321002

Reaction notes

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