alpha-Chloro-m-nitrotoluene → Methyl(3-nitrobenzyl)sulfane

HRID 2277738Notes

Reaction equation

HRID 2277738 reaction equation
[CH3:1][S-:2].[Na+].Cl[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=1>C(O)C>[CH3:1][S:2][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=1

Participants

4

Reactant 2

HCID 12078alpha-Chloro-m-nitrotolueneHCID 4378561Sodium methanethiolate

Product 1

HCID 22031873Methyl(3-nitrobenzyl)sulfaneYield 100.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium methanethiolate (13.5 g; 192 mmol) was added in two portions to a stirred solution of 1-(chloromethyl)-3-nitrobenzene (30.0 g; 175 mmol; Aldrich Chemical Company Inc.) in ethanol (360 mL) at −15° C. The cold bath was removed and the batch was stirred at room temperature for 3 hours. The batch was diluted with saturated aqueous sodium chloride solution and extracted with ethyl acetate (2×). The combined organic phases were washed with water, dried (sodium sulfate), filtered and concentrated to give the desired product (32.2 g) that was used without further purification.

Workup

  1. customThe cold bath was removed
  2. additionThe batch was diluted with saturated aqueous sodium chloride solution
  3. extractionextracted with ethyl acetate (2×)
  4. washThe combined organic phases were washed with water
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c6b94bc58baa4134b0ef5964add4422a
Source dataset
uspto-grants-2015_09
Patent number
US09133171B2

Reaction notes

Loading…