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

HRID 1707648Notes

Reaction equation

HRID 1707648 reaction equation
[OH-].[K+].[C:3]1([SH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.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)C=O>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([S:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=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)benzeneYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium hydroxide (6.15 g; 87%) was added to a stirred solution of thiophenol (10.0 g) in N,N-dimethylformamide (170 mL) at room temperature. When most of the potassium hydroxide appeared to have dissolved, 2,5-dichloronitrobenzene (17.4 g) was added, and the initially dark solution turned bright yellow with some precipitate. The reaction was placed in an oil bath at 70° C. for three hours, and then evaporated in vacuo. The residue was partitioned between chloroform and 1N NaOH and the layers were separated. The aqueous layer was extracted once more with chloroform. The chloroform solutions were combined, washed with 1N NaOH, H2O, 1N HCl, H2O and brine, dried over MgSO4, and evaporated in vacuo. The resulting oil was treated with cyclohexane, and the product crystallized. The crystalline product was collected by filtration, washed with hexane, and dried in vacuo at 56° C. to yield 13.73 g (57%) of yellow crystals. mp: 84°-86° C.

Workup

  1. dissolutionto have dissolved
  2. customevaporated in vacuo
  3. customThe residue was partitioned between chloroform and 1N NaOH
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted once more with chloroform
  6. washwashed with 1N NaOH, H2O, 1N HCl, H2O and brine
  7. dry with materialdried over MgSO4
  8. customevaporated in vacuo
  9. additionThe resulting oil was treated with cyclohexane
  10. customthe product crystallized
  11. filtrationThe crystalline product was collected by filtration
  12. washwashed with hexane
  13. customdried in vacuo at 56° C.

Sources & evidence

ORD record
ord-cac4e7e4df02489c9e164571b1805025
Source dataset
uspto-grants-1994_10
Patent number
US05354747

Reaction notes

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