Hydrochloric Acid → 2-[(2-Aminophenyl)sulfanyl]-4-nitrobenzoic acid

HRID 255923Notes

Reaction equation

HRID 255923 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].Cl[C:10]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13].N1C2C(=CC=CC=2)C=CC=1.Cl>O.N1C=CC=CC=1>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:10]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7047QuinolineHCID 74482-Chloro-4-nitrobenzoic acidHCID 87132-Aminothiophenol

Product 1

HCID 135363082-[(2-Aminophenyl)sulfanyl]-4-nitrobenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

Heat a mixture of 466 g (3.72 moles) of 2-aminothiophenol, 250 g (1.24 moles) of 2-chloro-4-nitrobenzoic acid, 1.25 liters of quinoline, 192 g (1.34 moles) of cuprous oxide and 125 ml of pyridine in an oil bath at 160°-170° C. with mechanical stirring for 90 minutes. Cool the mixture to room temperature and add 1.87 liters of concentrated hydrochloric acid followed by 625 ml of water. Separate the precipitate and wash well with water. Extract the washed precipitate into boiling methanol and filter. Treat the hot filtrate with charcoal, filter and strip to dryness. Dissolve the residue in aqueous sodium hydroxide, filter and treat with charcoal. Acidify the filtrate and separate the precipitate. (Yield: 38 g).

Workup

  1. temperatureHeat
  2. customSeparate the precipitate
  3. washwash well with water
  4. extractionExtract the washed precipitate
  5. filtrationfilter
  6. additionTreat the hot filtrate with charcoal
  7. filtrationfilter
  8. dissolutionDissolve the residue in aqueous sodium hydroxide
  9. filtrationfilter
  10. additiontreat with charcoal
  11. customseparate the precipitate

Sources & evidence

ORD record
ord-eab93a5f9b13495cb74a8d9d97bc309f
Source dataset
uspto-grants-1987_10
Patent number
US04699917

Reaction notes

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