Pyrazole → HCID 14053968, compound

HRID 622290Notes

Reaction equation

HRID 622290 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[CH:2]([CH3:4])[OH:3].[H-].[Na+].[H][H].[Cl:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=1[N:23]1[C:27](S(C)(=O)=O)=[C:26]([C:32]#[N:33])[CH:25]=[N:24]1.N1C=CC=N1>O1CCCC1>[Cl:12][C:13]1[CH:18]=[C:17]([C:19]([F:21])([F:22])[F:20])[CH:16]=[CH:15][C:14]=1[N:23]1[C:27]([O:3][CH:2]([C:1]([O:6][CH3:7])=[O:5])[CH3:4])=[C:26]([C:32]#[N:33])[CH:25]=[N:24]1

Participants

7

Reactant 5

HCID 1048Pyrazole2×HCID 11040Methyl Lactate2×HCID 24758Sodium hydride2×HCID 14053972HCID 14053972, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14053968HCID 14053968, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.1 g (0.011 mol) of methyl lactate are added dropwise to a suspension of 0.4 g (0.11 mol) of sodium hydride in 100 ml of anhydrous tetrahydrofuran. When the hydrogen evolution has ceased, a solution of 3.5 g (0.01 mol) of 1-(2-chloro-4-trifluoromethyl-phenyl)-4-cyano-5-methanesulphonyl-pyrazole (Ex. I-4) in tetrahydrofuran is added dropwise. After stirring at room temperature for 1 hour, some starting pyrazole can still be detected by thin-layer chromatography. After addition of a further 0.04 g of sodium hydride and 0.1 g of methyl lactate and stirring f 2 hours, starting pyrazole can no longer be detected by thin-layer chromatography. The reaction batch is concentrated in vacuo, the residue is distributed between water and methylene chloride, and the methylene chloride phase is washed with water, dried over sodium sulphate and concentrated in vacuo. The oily residue crystallizes overnight. After trituration with petroleum ether and filtering off, 2.3 g (62% of theory) of 1-(2-chloro-4-trifluoromethyl-phenyl)-4-cyano-5 -(1-methoxycarbonylethoxy)-pyrazole of melting point 82°-85° C. are obtained.

Workup

  1. stirringstirring f 2 hours
  2. concentrationThe reaction batch is concentrated in vacuo
  3. washthe methylene chloride phase is washed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe oily residue crystallizes overnight
  7. filtrationAfter trituration with petroleum ether and filtering off

Sources & evidence

ORD record
ord-9585963d6d2b4587b0057fff83195ffa
Source dataset
uspto-grants-1988_09
Patent number
US04770692

Reaction notes

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