4-Nitrophenyl methyl sulfide → HCID 59683178, compound

HRID 548957

Reaction equation

HRID 548957 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N-:11]Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.O.O.O.[Na+].[CH3:17][S:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1>C(#N)C.C(OCC)(=O)C>[CH3:17][S:18]([C:19]1[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=1)=[N:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

5

Reactant 2

HCID 961094-Nitrophenyl methyl sulfideHCID 517414chloramine-T trihydrate

Product 1

HCID 59683178HCID 59683178, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

10.0 g (35.3 mmol) of chloramine-T trihydrate (Aldrich) are added to 5.0 g (29.6 mmol) of 1-methylsulphanyl-4-nitrobenzene in 120 ml of acetonitrile at room temperature. The mixture is stirred at room temperature for 4 hours and then diluted with ethyl acetate. The mixture is filtered with suction and the filter cake is washed with ethyl acetate. The combined organic phases are dried (Na2SO4), filtered and concentrated. The resulting residue is recrystallized from methanol. 2.2 g (6.5 mmol; yield: 22%) of the product are obtained.

Workup

  1. filtrationThe mixture is filtered with suction
  2. washthe filter cake is washed with ethyl acetate
  3. dry with materialThe combined organic phases are dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue is recrystallized from methanol
  7. custom2.2 g (6.5 mmol; yield: 22%) of the product are obtained

Sources & evidence

ORD record
ord-46e8fd89e72b42cfa50550d8d73a9ec4
Source dataset
uspto-grants-2011_05
Patent number
US07943629B2

Linked notes

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