Triethylamine → HCID 13373963, compound

HRID 1632230Notes

Reaction equation

HRID 1632230 reaction equation
[CH3:1][N:2]1[C:6]([S:7][CH2:8][CH2:9][OH:10])=[C:5]([Cl:11])[C:4]([Cl:12])=[N:3]1.[CH3:13][S:14](Cl)(=[O:16])=[O:15].C(N(CC)CC)C>C(Cl)Cl>[CH3:1][N:2]1[C:6]([S:7][CH2:8][CH2:9][O:10][S:14]([CH3:13])(=[O:16])=[O:15])=[C:5]([Cl:11])[C:4]([Cl:12])=[N:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 13341318HCID 13341318, compound

Product 1

HCID 13373963HCID 13373963, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5 g (0.022 moles) 1-methyl-3,4-dichloro-5-(2-hydroxyethylthio)pyrazole and 2.52 g (0.022 moles) methane sulfonyl chloride in 100 ml methylene chloride was stirred at room temperature for two days. To that mixture, 2.4 g (3.3 ml) triethylamine was added. The reaction mixture was then stirred over the weekend. The mixture was filtered and the filtrate was washed with water, then dried over magnesium sulfate, and then cooled with dry ice. Stripping of the solvent, followed by chromatography on silica gel, eluting with 5% ethyl acetate/methylene chloride gave 5.1 g of the product as a viscous yellow oil.

Workup

  1. filtrationThe mixture was filtered
  2. washthe filtrate was washed with water
  3. dry with materialdried over magnesium sulfate
  4. temperaturecooled with dry ice
  5. washeluting with 5% ethyl acetate/methylene chloride

Sources & evidence

ORD record
ord-7c42f15b360941ca80591bbb2a49a8fc
Source dataset
uspto-grants-1984_10
Patent number
US04474797

Reaction notes

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