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Phosphorus pentachloride → HCID 178510205, compound

HRID 22864
Notes
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Reaction equation

HRID 22864 reaction equation
[C:1]([C:3]1[CH:7]=[C:6]([NH:8][C:9]([C:11]2[CH:16]=[N:15][CH:14]=[CH:13][N:12]=2)=O)[N:5]([C:17]2[C:22]([Cl:23])=[CH:21][C:20]([C:24]([F:27])([F:26])[F:25])=[CH:19][C:18]=2[Cl:28])[N:4]=1)#[N:2].P(Cl)(Cl)(Cl)(Cl)[Cl:30]>P(Cl)(Cl)(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[Cl:28][C:18]1[CH:19]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:22]([Cl:23])[C:17]=1[N:5]1[C:6](=[N:8][CH:9]([C:11]2[CH:16]=[N:15][CH:14]=[CH:13][N:12]=2)[Cl:30])[CH:7]=[C:3]([C:1]#[N:2])[NH:4]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 12137631N-[3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole-5-yl]pyrazine-2-carboxamide

Product 1

HCID 178510205HCID 178510205, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 24819Phosphorus pentachlorideCatalystHCID 1140Toluene
Solvent

Procedure

A mixture of 139 g (0.33 mol) of N-[3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole-5-yl]pyrazine-2-carboxamide, 72.6 g (0.35 mol) of phosphorus pentachloride, and 300 ml of toluene was heated under reflux for 2 hours. Further, 5 g of phosphorus pentachloride was added thereto, followed by heating under reflux for 1 hour. The mixture was cooled to room temperature and allowed to stand overnight. After stirring for 30 minutes, crystals were filtrated and washed with toluene. The crystals were dissolved in 1 L of chloroform and the solution was extracted after the addition of water. The organic layer was washed twice with water, and with saturated saline, and then, dried over anhydrous sodium sulfate. The solvent was removed by distillation and the resulting crystals were washed with hexane to obtain 112.3 g (yield 79%) of 1-(2,6-dichloro-4-trifluoromethylphenyl)-5-(pyrazin-2-ylchloromethylimino)pyrazole-3-carbonitrile.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. temperatureby heating
  4. temperatureunder reflux for 1 hour
  5. filtrationcrystals were filtrated
  6. washwashed with toluene
  7. dissolutionThe crystals were dissolved in 1 L of chloroform
  8. extractionthe solution was extracted
  9. additionafter the addition of water
  10. washThe organic layer was washed twice with water
  11. dry with materialwith saturated saline, and then, dried over anhydrous sodium sulfate
  12. customThe solvent was removed by distillation
  13. washthe resulting crystals were washed with hexane

Sources & evidence

ORD record
ord-5c5083b6d54f44909881dc618be3fee3
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06849633B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes