Sodium Thiosulfate → HCID 70976430, compound

HRID 1405205Notes

Reaction equation

HRID 1405205 reaction equation
C1(S[CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=2)CCCC1.ClC1[CH:23]=[CH:22][CH:21]=[C:20]([C:24](OO)=O)C=1.[S:28](=S)(=[O:31])([O-])[O-:29].[Na+].[Na+]>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[CH:20]1([S:28]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=2)(=[O:31])=[O:29])[CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 70976446HCID 70976446, compound

Product 1

HCID 70976430HCID 70976430, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1-[(cyclopentylsulfanyl)methyl]-3-nitrobenzene (4.5 g) in DCM (180 mL) was treated at 0° C. with portions of m-chloroperbenzoic acid (9.3 g, 77%). The mixture was stirred at 0° C. for further 90 minutes and then 18 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 (4.9 g).

Workup

  1. custom18 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-587d9ee664074c0bbe7335d6490740c4
Source dataset
uspto-grants-2014_12
Patent number
US08916557B2

Reaction notes

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