Water → HCID 19778083, compound

HRID 2082301Notes

Reaction equation

HRID 2082301 reaction equation
[CH3:1][N:2]1[C:6]([OH:7])=[C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=2)[C:4]([CH3:16])=[N:3]1.[Cl:17][C:18]1[N:23]=[C:22](Cl)[CH:21]=[CH:20][N:19]=1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[CH3:1][N:2]1[C:6]([O:7][C:20]2[CH:21]=[CH:22][N:23]=[C:18]([Cl:17])[N:19]=2)=[C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=2)[C:4]([CH3:16])=[N:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 775312,4-DichloropyrimidineHCID 178425688HCID 178425688, compound

Product 1

HCID 19778083HCID 19778083, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 10 ml of acetonitrile were dissolved 0.220 g (1.00 mmol) of 1,3-dimethyl-4-(3-methylphenoxy)-5-hydroxypyrazole, 0.220 g (1.50 mmol) of 2,4-dichloropyrimidine and 0.210 g (1.50 mmol) of potassium carbonate. Thus obtained solution was stirred for 3 hours with refluxing. After completing the reaction, the reaction solution was poured into water, extracted with ethyl acetate and dried. The organic layer was concentrated. The residue was purified by means of silica gel column chromatography (developing solution: ethyl acetate-hexane (1:1 v/v)) to give 0.29 g of 1,3-dimethyl-4-(3-methylphenoxy)-5-(2-chloropyrimidine-4-yloxy)pyrazole.

Workup

  1. temperaturewith refluxing
  2. customthe reaction
  3. extractionextracted with ethyl acetate
  4. customdried
  5. concentrationThe organic layer was concentrated
  6. customThe residue was purified by means of silica gel column chromatography (developing solution: ethyl acetate-hexane (1:1 v/v))

Sources & evidence

ORD record
ord-04fbe6e7ae954b1a95fd7937533c7e52
Source dataset
uspto-grants-1993_02
Patent number
US05189040

Reaction notes

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