Methanol → HCID 178499156, compound

HRID 1843070Notes

Reaction equation

HRID 1843070 reaction equation
[F:1][C:2]([F:19])([C:7]1[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([C:16]([OH:18])=[O:17])[NH:9][N:8]=1)[C:3]([F:6])([F:5])[F:4].S(Cl)(Cl)=O.[CH3:24]O>>[F:19][C:2]([F:1])([C:7]1[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([C:16]([O:18][CH3:24])=[O:17])[NH:9][N:8]=1)[C:3]([F:6])([F:5])[F:4]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 178524928HCID 178524928, compound

Product 1

HCID 178499156HCID 178499156, compound

Procedure

0.8 g (2.6 mmol) of 3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazol-5-carboxylic acid are dissolved in 15.0 ml of methanol and then slowly admixed dropwise with 0.58 ml (7.9 mmol) of thionyl chloride. The reaction solution is then heated under reflux for 16 hours. After cooling, the solvent is removed under reduced pressure on a rotary evaporator and the residue is taken up in ethyl acetate. The organic phase is carefully admixed with saturated sodium hydrogencarbonate solution. The organic phase is washed with saturated sodium chloride solution, dried over magnesium sulphate and filtered. The solvent is removed under reduced pressure on a rotary evaporator. This gives 0.75 g of methyl 3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxylate (96%) as a colourless oil.

Workup

  1. temperatureThe reaction solution is then heated
  2. temperatureunder reflux for 16 hours
  3. temperatureAfter cooling
  4. customthe solvent is removed under reduced pressure on a rotary evaporator
  5. washThe organic phase is washed with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customThe solvent is removed under reduced pressure on a rotary evaporator

Sources & evidence

ORD record
ord-8ee60e1fce8e45d58a2741bb70b6df3f
Source dataset
uspto-grants-2015_02
Patent number
US08946234B2

Reaction notes

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