Water → HCID 19778086, compound

HRID 2082299Notes

Reaction equation

HRID 2082299 reaction equation
[CH3:1][N:2]1[C:6]([OH:7])=[C:5]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[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]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[C:4]([CH3:16])=[N:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 775312,4-DichloropyrimidineHCID 178434080HCID 178434080, compound

Product 1

HCID 19778086HCID 19778086, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2.4 g (10 mmol) of 1,3-dimethyl-4-(2-chlorophenylthio)-5-hydroxypyrazole, 1.5 g (10 mmol) of 2,4-dichloropyrimidine and 1.5 g (11 mmol) of potassium carbonate was refluxed for 1 hour in 10 ml of acetonitrile. After completing the reaction, the reaction mixture was poured into water, extracted with ethyl acetate and dried. Then the organic layer was concentrated. The residue was purified by means of silica gel column chromatography (developing solution: ethyl acetate-hexane (3:1 v/v)) to give 2.8 g of 1,3-dimethyl-4-(2-chlorophenylthio)-5-(2-chloropyrimidine-4-yloxy)pyrazole

Workup

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

Sources & evidence

ORD record
ord-f24a06704d384b34aa9e353da2f1cbfb
Source dataset
uspto-grants-1993_02
Patent number
US05189040

Reaction notes

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