Water → HCID 15452060, compound

HRID 1005486Notes

Reaction equation

HRID 1005486 reaction equation
[Cl:1][C:2]1[C:3]([F:15])=[C:4]([C:8]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:10]=1)[C:5]([NH2:7])=O.P(Cl)(Cl)(Cl)=O.O>ClCCCl>[Cl:1][C:2]1[C:3]([F:15])=[C:4]([C:8]([C:11]([F:13])([F:14])[F:12])=[CH:9][CH:10]=1)[C:5]#[N:7]

Participants

5

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychloride2×HCID 27737483-Chloro-2-fluoro-6-(trifluoromethyl)benzamide

Product 1

HCID 15452060HCID 15452060, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
35 °C

Procedure

To a solution of 266 g of 3-chloro-2-fluoro-6-trifluoromethylbenzamide in 2.5 liters of 1,2-dichloroethane was added 339 g of phosphorus oxychloride and then the mixture was heated at reflux for 18.5 hours. After cooling, the solution was gradually added into 2 liters of water maintained at 30-40° C. to hydrolyze the excess amount of phosphorus oxychloride and was then separated. The aqueous layer was extracted with chloroform, and the extract was combined with the organic layer previously obtained, washed with IN aqueous solution of sodium hydroxide, water and saturated saline solution in series, and then dried over anhydrous magnesium sulfate. The solvent was distilled under reduced pressure, and the crude product obtained was washed with chilled n-hexane and then filtered to obtain 228 g of the title compound(mp. 43-44° C.).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 18.5 hours
  3. temperatureAfter cooling
  4. customwas then separated
  5. extractionThe aqueous layer was extracted with chloroform
  6. custompreviously obtained
  7. washwashed with IN aqueous solution of sodium hydroxide, water and saturated saline solution in series
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled under reduced pressure
  10. customthe crude product obtained
  11. washwas washed with chilled n-hexane
  12. filtrationfiltered

Sources & evidence

ORD record
ord-fa8f5083ab364df7a6deb7b5d19a85ee
Source dataset
uspto-grants-2000_04
Patent number
US06054605

Reaction notes

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