Ammonia → 2-Phenyl-3-phenylamino-benzo(b)thiophene

HRID 236796Notes

Reaction equation

HRID 236796 reaction equation
[C:1]1([S:7][CH:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:9](O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH3:18]>C1C=CC=CC=1>[C:12]1([C:8]2[S:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=3[C:9]=2[NH:18][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 2396052-Phenyl-2-(phenylsulfanyl)acetic acid

Product 1

HCID 166403612-Phenyl-3-phenylamino-benzo(b)thiophene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3.0 g of anilide of phenylthio-phenyl acetic acid (colourless needles in a mixture of benzene and petroleum ether mp 142°-143°) in 130 g of polyphosphoric acid are heated to 100° for 19 hours. The cooled reaction mixture is poured onto water, made alkaline by concentrated ammonia and extracted with methylene chloride. By drying over sodium sulphate and evaporating the extracts of methylene chloride, 1.7 g (60.0% of theory) of yellow oil are obtained which are recrystallized in ethanol: 1.5 g (45% of theory) of yellow crystals, mp 150°-151° (ethanol).

Workup

  1. temperatureare heated to 100° for 19 hours
  2. customThe cooled reaction mixture
  3. additionis poured onto water
  4. extractionextracted with methylene chloride
  5. dry with materialBy drying over sodium sulphate
  6. customevaporating the extracts of methylene chloride, 1.7 g (60.0% of theory) of yellow oil
  7. customare obtained which
  8. customare recrystallized in ethanol

Sources & evidence

ORD record
ord-72aa0048b1f947589c78b839a1434659
Source dataset
uspto-grants-1979_06
Patent number
US04157399

Reaction notes

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