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

HRID 275308Notes

Reaction equation

HRID 275308 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, 17 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. customis removed in vacuo
  2. customThe residue is partitioned between CHCl3 and N NaOH
  3. washThe organic layer is washed with N NaOH, H2O, N HCl, H2O
  4. dry with materialis dried over NaSO4 anhydrous
  5. filtrationfiltered
  6. customThe product is crystallized from cyclohexane

Sources & evidence

ORD record
ord-4cd405e6304f48d19003c16588a8d9b7
Source dataset
uspto-grants-1995_02
Patent number
US05393747

Reaction notes

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