Methanethiol → 1-(Methylsulfanyl)-4-nitro-2-(trifluoromethyl)benzene

HRID 2052422Notes

Reaction equation

HRID 2052422 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[CH:6]=[CH:7][C:8]=1Cl.[CH3:15][SH:16].[OH-].[Na+]>CS(C)=O.O>[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[CH:6]=[CH:7][C:8]=1[S:16][CH3:15]

Participants

6

Reactant 3

HCID 878MethanethiolHCID 14798Sodium HydroxideHCID 612132-Chloro-5-nitrobenzotrifluoride

Product 1

HCID 123270521-(Methylsulfanyl)-4-nitro-2-(trifluoromethyl)benzeneYield 95%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a stirred solution containing 45.1 g (0.20 mole) of 3-(trifluoromethyl)-4-chloronitrobenzene and 15 g (0.30 mole) of methyl mercaptan in 150 ml of DMSO was added dropwise at ambient temperature a solution containing 8.0 g (0.20 mole) of sodium hydroxide in 20 ml of water. This addition was exothermic to 60° C. After one hour, the reaction mixture was poured into ice water. The product was filtered and dried to give 45.0 g (95%) of yellow solid; m.p. 50° C.

Workup

  1. additionwas added dropwise at ambient temperature a solution
  2. additionThis addition
  3. customwas exothermic to 60° C
  4. filtrationThe product was filtered
  5. customdried

Sources & evidence

ORD record
ord-2354fd5517ac4829bf1f9b3038a12c83
Source dataset
uspto-grants-1980_01
Patent number
US04184867

Reaction notes

Loading…