Sodium Thiosulfate → HCID 70976411, compound

HRID 1405210Notes

Reaction equation

HRID 1405210 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([CH2:11]SC)[CH:3]=1.Cl[C:15]1C=CC=C(C(OO)=O)C=1.[S:25](=S)(=[O:28])([O-])[O-:26].[Na+].[Na+]>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([CH2:11][S:25]([CH3:15])(=[O:28])=[O:26])[CH:3]=1

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 70976465HCID 70976465, compound

Product 1

HCID 70976411HCID 70976411, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1-chloro-3-[(methylsulfanyl)methyl]-5-nitrobenzene (4.26 g) in DCM (190 mL) was treated at 0° C. with portions of m-chloroperbenzoic acid (8.77 g, 77%). The mixture was stirred at 0° C. for further 30 minutes and then 17 hours at room temperature. The reaction mixture was diluted with DCM before disodium sulfurothioate and sodium bicarbonate solution was added and extracted with DCM (2×). The combinded organic phases were washed and concentrated. The residue was purified by chromatography (hexane/ethyl acetate 12% 100%) to give the title compound (4.80 g). An analytical sample was crystallized from acetone/hexan.

Workup

  1. custom17 hours
  2. customat room temperature
  3. additionwas added
  4. extractionextracted with DCM (2×)
  5. washThe combinded organic phases were washed
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (hexane/ethyl acetate 12% 100%)

Sources & evidence

ORD record
ord-be6cd2bdabab46b484c059dd88005957
Source dataset
uspto-grants-2014_12
Patent number
US08916557B2

Reaction notes

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