Methanethiol → 4-Nitrophenyl methyl sulfide

HRID 1701974Notes

Reaction equation

HRID 1701974 reaction equation
[CH3:1][SH:2].[OH-].[K+].Cl[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1>CN(C)C=O.C(O)C>[CH3:1][S:2][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 878MethanethiolHCID 74741-Chloro-4-nitrobenzeneHCID 14797Potassium Hydroxide

Product 1

HCID 961094-Nitrophenyl methyl sulfide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

28.3 g of methylmercaptan are dissolved in 500 ml of dimethylformamide at 0° C., under nitrogen. 37.4 g of potassium hydroxide, dissolved in 150 ml of ethanol, are then added dropwise at -10° C., after which 94.5 g of 4-chloronitrobenzene are added. The reaction mixture is warmed to 100° C. and stirred at this temperature for 8 hours. It is then stirred into 5 kg of ice water. The precipitate is filtered off with suction, washed, dried and recrystallised from methanol. Yield: 86.2 g of yellow crystals of melting point 71°-73.5° C.

Workup

  1. additionare then added dropwise at -10° C.
  2. filtrationThe precipitate is filtered off with suction
  3. washwashed
  4. customdried
  5. customrecrystallised from methanol

Sources & evidence

ORD record
ord-ec799eca64ce4c27b444597031437d2b
Source dataset
uspto-grants-1983_04
Patent number
US04379819

Reaction notes

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