Dimethyl Sulfate → 4-(2,4-dichlorobenzoyl)-1,3-dimethyl-5-[2-(N-methylanilino)ethoxy]pyrazole

HRID 1462396Notes

Reaction equation

HRID 1462396 reaction equation
[NH:1]([CH2:8][CH2:9][O:10][C:11]1[N:15]([CH3:16])[N:14]=[C:13]([CH3:17])[C:12]=1[C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=1[Cl:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(OC)(O[CH3:32])(=O)=O>C1C=CC=CC=1>[Cl:26][C:20]1[CH:21]=[C:22]([Cl:25])[CH:23]=[CH:24][C:19]=1[C:18]([C:12]1[C:13]([CH3:17])=[N:14][N:15]([CH3:16])[C:11]=1[O:10][CH2:9][CH2:8][N:1]([CH3:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:27]

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 13277505HCID 13277505, compound

Product 1

HCID 132775064-(2,4-dichlorobenzoyl)-1,3-dimethyl-5-[2-(N-methylanilino)ethoxy]pyrazole

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2.7 g of 5-(2-anilinoethoxy)-4-(2,4-dichlorobenzoyl)-1,3-dimethylpyrazole prepared by the procedure of Example 1 or 3 was dissolved in 25 ml of benzene, then 0.7 ml of dimethyl sulphate was added and the mixture heated under reflux for 3 hours with stirring. After cooling of the mixture and washing with water, the organic layer was dried over anhydrous sodium sulphate and the solvent distilled off to give 2.4 g of the desired product, Compound 2, similar to that of Examples 2 and 3 (yield 86%).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling of the mixture
  4. washwashing with water
  5. dry with materialthe organic layer was dried over anhydrous sodium sulphate
  6. distillationthe solvent distilled off

Sources & evidence

ORD record
ord-99258edf0cb347d5a9e6619ed48f8830
Source dataset
uspto-grants-1984_07
Patent number
US04460597

Reaction notes

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