Triethylamine → HCID 178503239, compound

HRID 609536Notes

Reaction equation

HRID 609536 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[S:12][CH3:13].[CH:14]1([C:17]2[CH:21]=[C:20]([OH:22])[N:19]([CH3:23])[N:18]=2)[CH2:16][CH2:15]1.C(N(CC)CC)C.[C:31](=O)([O-])[O-:32].[K+].[K+]>O1CCOCC1>[CH:14]1([C:17]2[C:21]([C:31](=[O:32])[C:2]3[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=3[S:12][CH3:13])=[C:20]([OH:22])[N:19]([CH3:23])[N:18]=2)[CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 19599111(2-Iodo-5-(trifluoromethyl)phenyl)(methyl)sulfaneHCID 178481725HCID 178481725, compound

Product 1

HCID 178503239HCID 178503239, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Into a 200 ml autoclave, 1.59 g of 4-iodo-3-methylthiobenzotrifluoride prepared in accordance with the following Preparation Example 10, 1.38 g of 3-cyclopropyl-5-hydroxy-1-methylpyrazole (after-mentioned Intermediate No. 1a-1), 0.5 g of triethylamine, 3.1 g of potassium carbonate, 0.22 g of palladium (II) bis-triphenylphosphine) dichloride and 40 ml of dioxane were put and sealed, and the interior of the autoclave was flushed with carbon monoxide (pressure: 65 kg/cm2), followed by a reaction at 140° C. for 8 hours. After completion of the reaction, the solvent was distilled off, and the residue was dissolved in water, and then insoluble matters were filtered off. The filtrate was washed with dichloromethane. The washed product was acidified (pH=1) with concentrated hydrochloric acid and extracted with dichloromethane. The obtained extract solution was dried over anhydrous sodium sulfate, and the solvent was distilled off to obtain 1.59 g of 3-cyclopropyl-1-methyl-4-(2-methylthio-4-trifluoromethylbenzoyl)-5-hydroxypyrazole (after-mentioned Compound No. a-82) as a reddish brown solid.

Workup

  1. customsealed
  2. customthe interior of the autoclave was flushed with carbon monoxide (pressure: 65 kg/cm2)
  3. customfollowed by a reaction at 140° C. for 8 hours
  4. customAfter completion of the reaction
  5. distillationthe solvent was distilled off
  6. dissolutionthe residue was dissolved in water
  7. filtrationinsoluble matters were filtered off
  8. washThe filtrate was washed with dichloromethane
  9. extractionextracted with dichloromethane
  10. extractionThe obtained extract solution
  11. dry with materialwas dried over anhydrous sodium sulfate
  12. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-8b46b6be1f6048e5a957e711e89a2524
Source dataset
uspto-grants-1999_12
Patent number
US05998334

Reaction notes

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