2-Propanethiol → 4-Nitro-1-[(propan-2-yl)sulfanyl]-2-(trifluoromethyl)benzene

HRID 2052423Notes

Reaction equation

HRID 2052423 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[CH:15]([SH:18])([CH3:17])[CH3:16].[OH-].[Na+]>CS(C)=O>[CH:15]([S:18][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 63642-PropanethiolHCID 14798Sodium HydroxideHCID 612132-Chloro-5-nitrobenzotrifluoride

Product 1

HCID 123270534-Nitro-1-[(propan-2-yl)sulfanyl]-2-(trifluoromethyl)benzeneYield 99.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution containing 112.8 g (0.5 mole) of 2-chloro-5-nitrobenzotrifluoride and 46 g (0.6 mole) of isopropyl mercaptan in 400 ml of DMSO was added dropwise over 0.5 hour 40 g of 50% aqueous sodium hydroxide. This addition was exothermic to 50° C. After 24 hours, the reaction mixture was poured into ice water and extracted with 3×200 ml of methylene chloride. The combined extracts were washed with water, dried and concentrated to give 132 g (99%) of product as an orange liquid.

Workup

  1. additionThis addition
  2. customwas exothermic to 50° C
  3. extractionextracted with 3×200 ml of methylene chloride
  4. washThe combined extracts were washed with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7fbc8fc08bcd40e39ff3a45591ab0b7d
Source dataset
uspto-grants-1980_01
Patent number
US04184867

Reaction notes

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