Water → (3-Nitrobenzyl)(propyl)sulfane

HRID 1256150Notes

Reaction equation

HRID 1256150 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=1.[CH2:12]([S-:15])[CH2:13][CH3:14].[Na+].O>CN(C=O)C>[N+:9]([C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[CH2:2][S:15][CH2:12][CH2:13][CH3:14])([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 962WaterHCID 12078alpha-Chloro-m-nitrotolueneHCID 46817251-Propanethiol, sodium salt (1:1)

Product 1

HCID 67173878(3-Nitrobenzyl)(propyl)sulfaneYield 91.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 1-(chloromethyl)-3-nitrobenzene (10.0 g, 58.1 mmol) in DMF (30 mL) was stirred at room temperature, then sodium propane-1-thiolate (5.7 g, 58.1 mmol) was added, followed by stirring at 60° C. overnight. After water was added, the aqueous layer was extracted with ethyl acetate 3 times. The combined organic phase was washed with brine, dried over sodium sulfate and concentrated to give (3-nitrobenzyl)(propyl)sulfane (11.2 g, yield 91%).

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate 3 times
  2. washThe combined organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3f06213bfa9f4e0b9899ac993d41d6e2
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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