Methanesulfonyl chloride → HCID 57518524, compound

HRID 1020883Notes

Reaction equation

HRID 1020883 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][OH:8])[CH:3]=[N:2]1.[CH3:9][S:10](Cl)(=[O:12])=[O:11].C(N(CC)C(C)C)(C)C>ClCCl>[CH3:9][S:10]([O:8][CH2:7][CH2:6][C:4]1[CH:5]=[N:1][N:2]([S:10]([CH3:9])(=[O:12])=[O:11])[CH:3]=1)(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 42936042-(1H-Pyrazol-4-yl)ethanol

Product 1

HCID 57518524HCID 57518524, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-(1H-pyrazol-4-yl)ethanol (50 mg, 0.45 mmol) in dichloromethane (3 mL) at 0° C. was added methanesulfonyl chloride (0.104 mL, 1.39 mmol) followed by N,N-diisopropylethylamine (0.312 mL, 1.78 mmol) dropwise. The ice bath was removed and the mixture warmed to ambient temperature and stirred for 1 h. The solvent was removed in vacuo and the residue purified by column chromatography (silica gel Biotage 25S) eluting with ethyl acetate/hexane (gradient from 0% to 100%) to give the title compound as a colorless solid. LC/MS 269.2 (M+1).

Workup

  1. customThe ice bath was removed
  2. customThe solvent was removed in vacuo
  3. customthe residue purified by column chromatography (silica gel Biotage 25S)
  4. washeluting with ethyl acetate/hexane (gradient from 0% to 100%)

Sources & evidence

ORD record
ord-1cb4e121010c496d9a2eb466ba4b4a56
Source dataset
uspto-grants-2014_05
Patent number
US08716482B2

Reaction notes

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