Methanesulfonyl chloride → HCID 59401155, compound

HRID 77061Notes

Reaction equation

HRID 77061 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH:4]([OH:11])[C:5]1[S:6][C:7]([CH3:10])=[CH:8][CH:9]=1.C(N(C(C)C)C(C)C)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[CH:4]([O:11][S:23]([CH3:22])(=[O:25])=[O:24])[C:5]1[S:6][C:7]([CH3:10])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 59401096HCID 59401096, compound

Product 1

HCID 59401155HCID 59401155, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of hydroxy-(5-methyl-thiophen-2-yl)-acetic acid methyl ester (I265) (1.84 g, 9.89 mmol) in dry DCM, cooled at 0° C. under nitrogen atmosphere, N-ethyl-N-isopropylpropan-2-amine (2.54 mL, 14.8 mmol) and methanesulfonyl chloride (1.16 mL, 14.8 mmol) are added and the reaction is stirred at RT for 2 hours. DCM is added and the organic phase is washed with aq. NaHCO3, water and brine, dried over Na2SO4 and evaporated to obtain intermediate I268 as a dark brown oil (2.1 g, 80% yield).

Workup

  1. washthe organic phase is washed with aq. NaHCO3, water and brine
  2. dry with materialdried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-55526f809b09481692e24c02781263b8
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Reaction notes

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