1-Chloro-2,4-Dinitrobenzene → 1-(4-(Methylthio)phenoxy)-2,4-dinitrobenzene

HRID 2164648Notes

Reaction equation

HRID 2164648 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[OH-].[Na+].[N+:12]([C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1Cl)([O-:14])=[O:13]>S1(CCCC1)(=O)=O>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][C:16]2[CH:17]=[CH:18][C:19]([N+:21]([O-:23])=[O:22])=[CH:20][C:15]=2[N+:12]([O-:14])=[O:13])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 61-Chloro-2,4-DinitrobenzeneHCID 140864-(Methylthio)phenolHCID 14798Sodium Hydroxide

Product 1

HCID 130785271-(4-(Methylthio)phenoxy)-2,4-dinitrobenzeneYield 97.4%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 15.4 g (0.110 mole) of 4-(methylthio)phenol dissolved in 150 ml of sulfolane was added 4.40 g (0.110 mole) of NaOH. The mixture was heated to 65° C. and 20.25 g (0.100 mole) of 2,4-dinitrochlorobenzene added and the reaction mixture heated at 65° C. for 3.25 hrs. The product was recovered (29.8 g, 97.4% yield) as described in Example 1 and recrystallized from ethanol, which gave purified 1-(4-(methylthio)phenoxy)-2,4-dinitrobenzene, mp 119°-120.5° C.

Workup

  1. temperaturethe reaction mixture heated at 65° C. for 3.25 hrs
  2. customThe product was recovered (29.8 g, 97.4% yield)
  3. customrecrystallized from ethanol, which
  4. customgave
  5. custompurified 1-(4-(methylthio)phenoxy)-2,4-dinitrobenzene, mp 119°-120.5° C.

Sources & evidence

ORD record
ord-ed17524adfd54e089493526d6170af2c
Source dataset
uspto-grants-1985_03
Patent number
US04505929

Reaction notes

Loading…