tert-Butyl mercaptan → 1,2,4,5-Tetrakis(tert-butylthio)benzene

HRID 1048731

Reaction equation

HRID 1048731 reaction equation
[Na].[CH3:2][C:3]([SH:6])([CH3:5])[CH3:4].Cl[C:8]1[CH:13]=[C:12](Cl)[C:11](Cl)=[CH:10][C:9]=1Cl>CN(C=O)C>[C:3]([S:6][C:8]1[CH:13]=[C:12]([S:6][C:3]([CH3:5])([CH3:4])[CH3:2])[C:11]([S:6][C:3]([CH3:5])([CH3:4])[CH3:2])=[CH:10][C:9]=1[S:6][C:3]([CH3:5])([CH3:4])[CH3:2])([CH3:5])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 6387tert-Butyl mercaptanHCID 72701,2,4,5-TetrachlorobenzeneHCID 5360545Sodium

Product 1

HCID 118120541,2,4,5-Tetrakis(tert-butylthio)benzeneYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium (9.3 g, 0.18 mol) was added to a degassed solution of 2-methyl-2-propanethiol (20.9 mL, 0.18 mol) in dry DMF (105 mL), under stirring at 0° C. in nitrogen atmosphere. The mixture was allowed to reach room temperature (RT, 20-25° C.) and stirred overnight. 1,2,4,5-Tetrachlorobenzene (8.0 g, 0.037 mol) was then added and the resulting mixture was stirred at RT for 2 h and then gently refluxed for 18 h. After cooling at RT, the reaction mixture was poured over ice (100 g), the precipitate was removed by filtration, washed with water, and dried to give 11.0 g of the title compound as an off-white powder.

Workup

  1. customto reach room temperature
  2. custom(RT, 20-25° C.)
  3. stirringstirred overnight
  4. stirringthe resulting mixture was stirred at RT for 2 h
  5. temperaturegently refluxed for 18 h
  6. temperatureAfter cooling at RT
  7. customthe precipitate was removed by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-87b806a754504fe39d1e651f26080e47
Source dataset
uspto-grants-2016_07
Patent number
US09381257B2

Linked notes

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