Water → 1-(2-Methylsulfonyloxyethyl)-5-formamidopyrazole

HRID 1681646Notes

Reaction equation

HRID 1681646 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:8]([NH:9][CH:10]=[O:11])=[CH:7][CH:6]=[N:5]1.C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21].O>C(Cl)Cl>[CH3:19][S:20]([O:1][CH2:2][CH2:3][N:4]1[C:8]([NH:9][CH:10]=[O:11])=[CH:7][CH:6]=[N:5]1)(=[O:22])=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 150777375-Formamido-1-(2-hydroxyethyl)pyrazole

Product 1

HCID 150777381-(2-Methylsulfonyloxyethyl)-5-formamidopyrazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(2-hydroxyethyl)-5-formamidopyrazole (10 g) and triethylamine (18 ml) in methylene chloride (100 ml) was added dropwise methanesulfonyl chloride (8.5 ml) under ice-cooling. The mixture was stirred at 0° C. for 1.5 hours. The reaction mixture was poured into water (20 ml) and the methylene chloride layer was separated. The aqueous layer was reextracted with tetrahydrofuran twice. The organic layers were combined and dried over magnesium sulfate. The solvent was evaporated and the residue was subjected to column chromatography on silica gel (200 g) using ethyl acetate as an eluent. Fractions containing the object compound were combined and evaporated in vacuo to give 1-(2-methylsulfonyloxyethyl)-5-formamidopyrazole (3.2 g) as crystals.

Workup

  1. temperaturecooling
  2. customthe methylene chloride layer was separated
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated
  5. additionFractions containing the object compound
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-520796391dd44fefa81355fdbb215376
Source dataset
uspto-grants-1992_12
Patent number
US05173485

Reaction notes

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