Water → HCID 19993699, compound

HRID 345115Notes

Reaction equation

HRID 345115 reaction equation
[C:1]([C:4]1[C:8]([O:9][C:10]([F:15])([F:14])[CH:11]([Cl:13])[F:12])=[CH:7][N:6]([C:16]2[C:21]([Cl:22])=[CH:20][C:19]([C:23]([F:26])([F:25])[F:24])=[CH:18][C:17]=2[Cl:27])[N:5]=1)(=O)[NH2:2].P(Cl)(Cl)(Cl)=O.O>ClCCl>[Cl:13][CH:11]([F:12])[C:10]([F:15])([F:14])[O:9][C:8]1[C:4]([C:1]#[N:2])=[N:5][N:6]([C:16]2[C:21]([Cl:22])=[CH:20][C:19]([C:23]([F:26])([F:24])[F:25])=[CH:18][C:17]=2[Cl:27])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 19993702HCID 19993702, compound

Product 1

HCID 19993699HCID 19993699, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (RS)-3-carbamoyl-4-(2-chloro-1,1,2-trifluoroethoxy)-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (0.75g) and phosphorus oxychloride (15ml) was heated at 80° C. for 6 hours. Water (100ml) and dichloromethane (50ml) were added to the cooled mixture and the layers were separated. The aqueous layer was extracted with dichloromethane (2x50ml) and the combined organic layers were washed with aqueous sodium hydrogen carbonate solution (1M; 30ml), dried over magnesium sulfate, and evaporated to give (RS)-4-(2-chloro-1,1,2-trifluoroethoxy)-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyanopyrazole (0.4g) as an off-white crystalline solid, m.p. 99°-101° C.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with dichloromethane (2x50ml)
  3. washthe combined organic layers were washed with aqueous sodium hydrogen carbonate solution (1M; 30ml)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-ef51c71e917a45d2aaad982ed610f0af
Source dataset
uspto-grants-1991_10
Patent number
US05055482

Reaction notes

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