2,5-Dichloronitrobenzene → 4-Chloro-2-nitro-1-(phenylthio)benzene

HRID 1646900Notes

Reaction equation

HRID 1646900 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].Cl[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19]>CN(C=O)C>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:12]([N+:18]([O-:20])=[O:19])[CH:13]=1

Participants

5

Reactant 3

HCID 69772,5-DichloronitrobenzeneHCID 7969ThiophenolHCID 14797Potassium Hydroxide2×

Product 1

HCID 3769774-Chloro-2-nitro-1-(phenylthio)benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirring solution of 10.0 g (91 mmol) of thiophenol in 170 mL of DMF is added 6.2 g (95 mmol) of KOH. When the KOH has dissolved, i7 g (91 mmol) of 2,5-dichloronitrobenzene is added. After stirring for 3 hours at 70° C., the solvent is removed in vacuo. The residue is partitioned between CHCl3 and N NaOH. The organic layer is washed with N NaOH, H2O, N HCl, H2O and is dried over NaSO4 anhydrous, filtered, and stripped. The product is crystallized from cyclohexane.

Workup

  1. additionis added
  2. customthe solvent is removed in vacuo
  3. customThe residue is partitioned between CHCl3 and N NaOH
  4. washThe organic layer is washed with N NaOH, H2O, N HCl, H2O
  5. dry with materialis dried over NaSO4 anhydrous
  6. filtrationfiltered
  7. customThe product is crystallized from cyclohexane

Sources & evidence

ORD record
ord-2344f9d46821424bbd891b9577c2d488
Source dataset
uspto-grants-1993_01
Patent number
US05182272

Reaction notes

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