2-Nitro-4'-chloro diphenyl sulfide → 2-[(4-Chlorophenyl)sulfanyl]aniline

HRID 2185931Notes

Reaction equation

HRID 2185931 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-])=O)=[CH:4][CH:3]=1.[Sn]>C(O)(=O)C.Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH2:15])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 3653942-Nitro-4'-chloro diphenyl sulfideHCID 5352426Tin atom

Product 1

HCID 3612972-[(4-Chlorophenyl)sulfanyl]anilineYield 99.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

2-(4-Chlorophenylthio)nitrobenzene (1.0 g) was dissolved in a mixture of acetic acid (5 ml) and 6N hydrochloride (5 ml), and tin (1.0 g) was added thereto, followed by stirring for six hours at room temperature. After the solvent was removed under reduced pressure, the residue was dissolved in water (50 ml) and a pH of the resultant solution was adjusted to 9-10 with potassium carbonate. The thus-obtained solution was extracted with ethyl acetate. The extracted solution was washed sequentially with water and saturated brine and dried over anhydrous sodium sulfate. Subsequently, the solvent was removed under reduced pressure and the residue was crystallized from ethyl acetate under stirring, to thereby yield the target compound (880 mg) as pale-yellow crystals.

Workup

  1. additionwas added
  2. customAfter the solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in water (50 ml)
  4. extractionThe thus-obtained solution was extracted with ethyl acetate
  5. washThe extracted solution was washed sequentially with water and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customSubsequently, the solvent was removed under reduced pressure
  8. customthe residue was crystallized from ethyl acetate
  9. stirringunder stirring

Sources & evidence

ORD record
ord-6cfb0af81ac04dfa86555dec623ce70a
Source dataset
uspto-grants-2002_06
Patent number
US06403607B1

Reaction notes

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