Water → HCID 14838486, compound

HRID 1381545Notes

Reaction equation

HRID 1381545 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]1[CH:14]=[CH:13][NH:12][N:11]=1.[OH-].[K+].[CH3:17]I.O>CS(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]1[CH:14]=[CH:13][N:12]([CH3:17])[N:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 178489578HCID 178489578, compound

Product 1

HCID 14838486HCID 14838486, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The pyrazole from Example 5 (b) (4.0 g) was added to a mixture of crushed potassium hydroxide pellets (4.7 g) in dry dimethylsulphoxide, which had previously been stirred for 5 minutes under nitrogen at room temperature. After stirring for 0.75 hours, methyl iodide (3.1 g) was added to the red solution and stirring was maintained for a further 0.75 hours. The reaction mix was poured into water, extracted with ethyl acetate, the organic layer washed, dried, evaporated and chromatographed to give a light brown oil.

Workup

  1. stirringAfter stirring for 0.75 hours
  2. stirringstirring
  3. temperaturewas maintained for a further 0.75 hours
  4. additionThe reaction mix
  5. extractionextracted with ethyl acetate
  6. washthe organic layer washed
  7. customdried
  8. customevaporated
  9. customchromatographed
  10. customto give a light brown oil

Sources & evidence

ORD record
ord-27a3ed433f4542ce95aeb5a1af5b534f
Source dataset
uspto-grants-1989_02
Patent number
US04803216

Reaction notes

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