2-Propanethiol → HCID 20376632, compound

HRID 2052426Notes

Reaction equation

HRID 2052426 reaction equation
Cl[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH:12]([SH:15])([CH3:14])[CH3:13].[OH-].[Na+]>CS(C)=O.O>[CH:12]([S:15][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10])([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 63642-PropanethiolHCID 124774-Chloro-3-nitroanilineHCID 14798Sodium Hydroxide

Product 1

HCID 20376632HCID 20376632, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution containing 34.5 g (0.20 mole) of 4-chloro-3-nitroaniline and 24 g (0.30 mole) of isopropyl mercaptan in 200 ml of DMSO was added dropwise at ambient temperature a solution of 8.0 g (0.20 mole) of sodium hydroxide in 10 ml of water. The addition was exothermic to 60° and the mixture became deep red in color. After three days, the reaction mixture was poured into water and extracted with methylene chloride. The combined extracts were washed with water, dried with anhydrous MgSO4, filtered and concentrated to give 41.1 g (97%) of product as a red-brown syrup.

Workup

  1. additionThe addition
  2. customwas exothermic to 60°
  3. extractionextracted with methylene chloride
  4. washThe combined extracts were washed with water
  5. dry with materialdried with anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6b041978ae9e45b8b118931145febe12
Source dataset
uspto-grants-1980_01
Patent number
US04184867

Reaction notes

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