Hydroxyethyl disulfide → 2-Methanesulfonyloxyethyl disulfide

HRID 1840426

Reaction equation

HRID 1840426 reaction equation
C(N(CC)C(C)C)(C)C.[CH3:10][S:11](Cl)(=[O:13])=[O:12].[OH:15][CH2:16][CH2:17][S:18][S:19][CH2:20][CH2:21][OH:22]>ClCCl>[CH3:10][S:11]([O:15][CH2:16][CH2:17][S:18][S:19][CH2:20][CH2:21][O:22][S:11]([CH3:10])(=[O:13])=[O:12])(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 15906Hydroxyethyl disulfideHCID 31297Methanesulfonyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 231172092-Methanesulfonyloxyethyl disulfide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N,N-Diisopropylethylamine (4.35 ml) and 1.70 ml of methanesulfonyl chloride were added to a suspension of 1.22 ml of 2-hydroxyethyl disulfide in 30 ml of dichloromethane at −40° C. under an argon atmosphere. The mixture was stirred at that temperature for 30 min. The reaction solution was then diluted with dichloromethane, and the diluted solution was washed with an dilute aqueous hydrochloric acid solution, an aqueous sodium hydrogencarbonate solution, and water in that order, and was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure to prepare 3.08 g of 2-methanesulfonyloxyethyl disulfide.

Workup

  1. washthe diluted solution was washed with an dilute aqueous hydrochloric acid solution
  2. dry with materialan aqueous sodium hydrogencarbonate solution, and water in that order, and was dried over anhydrous magnesium sulfate
  3. customThe solvent was removed by distillation under the reduced pressure
  4. customto prepare 3.08 g of 2-methanesulfonyloxyethyl disulfide

Sources & evidence

ORD record
ord-d13d244bb92a4400a4f1dbd341cc93ce
Source dataset
uspto-grants-2004_01
Patent number
US06680313B2

Linked notes

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