Phosphorus oxychloride → HCID 74014582, compound

HRID 1167165Notes

Reaction equation

HRID 1167165 reaction equation
[I:1][C:2]1[S:6][C:5]([NH:7][C:8](=O)[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)=[N:4][C:3]=1[C:20]([F:23])([F:22])[F:21].P(Cl)(Cl)(Cl)(Cl)[Cl:25].P(Cl)(Cl)(Cl)=O>>[I:1][C:2]1[S:6][C:5]([N:7]=[C:8]([Cl:25])[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)=[N:4][C:3]=1[C:20]([F:23])([F:22])[F:21]

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 22996146HCID 22996146, compound

Product 1

HCID 74014582HCID 74014582, compound

Procedure

N-(5-Iodo-4-trifluoromethylthiazol-2-yl)-3-trifluoromethylbenzamide (9.3 g was mixed with phosphorous pentachloride (4.2 g) and phosphorous oxychloride (25 ml) and the mixture was refluxed for 7 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 chloroform-n-hexane to give N-(5-iodo-4-trifluoromethylthiazol-2-yl)-3-trifluoromethylbenzimidoyl chloride as yellow needles (8.5 g), m. p. 136-137° C.

Workup

  1. temperaturethe mixture was refluxed for 7 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 chloroform-n-hexane

Sources & evidence

ORD record
ord-dbfa6fdd9a46442b9e3b5965c445fc42
Source dataset
uspto-grants-2003_09
Patent number
US06617341B1

Reaction notes

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