Phosphorus pentachloride → HCID 74014581, compound

HRID 1167166Notes

Reaction equation

HRID 1167166 reaction equation
[Cl:1][C:2]1[S:6][C:5]([NH:7][C:8](=O)[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)=[N:4][C:3]=1[C:17]([F:20])([F:19])[F:18].P(Cl)(Cl)(Cl)(Cl)[Cl:22]>P(Cl)(Cl)(Cl)=O>[Cl:1][C:2]1[S:6][C:5]([N:7]=[C:8]([Cl:22])[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)=[N:4][C:3]=1[C:17]([F:20])([F:19])[F:18]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 22996144HCID 22996144, compound

Product 1

HCID 74014581HCID 74014581, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

N-(5-Chloro-4-trifluoromethylthiazol-2-yl)-3-chlorobenzamide (15.5 g was mixed with phosphorous pentachloride (9.5 g) and phosphorous oxychloride (60 ml) and the mixture was refluxed for 12 hr. The excess phosphorous oxychloride was removed under reduced pressure and the residue was mixed with cold water then extracted with chloroform. The extract was dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure then the residue was recrystallized from n-hexane to give N-(5-chloro-4-trifluoromethylthiazol-2-yl)-3-chlorobenzimidoyl chloride; as pale brown needles (11.0 g), m. p. 89-90° C.

Workup

  1. temperaturethe mixture was refluxed for 12 hr
  2. customThe excess phosphorous oxychloride was removed under reduced pressure
  3. additionthe residue was mixed with cold water
  4. extractionthen extracted with chloroform
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customthe residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-5ff4b339e7cc45bd815b6d60ce78c12d
Source dataset
uspto-grants-2003_09
Patent number
US06617341B1

Reaction notes

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