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

HRID 236795

Reaction equation

HRID 236795 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.[C:18]1(C)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[NH3:39]>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:39][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 1140TolueneHCID 14812Phosphorus oxide (P4O10)HCID 2396052-Phenyl-2-(phenylsulfanyl)acetic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 9.6 g (30 mmol) of anilide of α-phenylthio-phenylacetic acid (colourless needles in a mixture of benzene and petroleum ether, mp 142°-143°), 70 milliliters of absolute toluene and 30.0 g (211 mmol) of phosphoric anhydride is stirred at 100° for 8 hours. The cooled reaction mixture is poured onto ice, made alkaline by concentrated ammonia and extracted with methylene chloride. By drying over sodium sulphate and evaporating the organic phase, 8.9 g (98.4% of theory) of crude product are obtained which are recrystallised in ethanol: 5.7 g (64% of theory) of yellow crystals, mp 150°-151° (ethanol).

Workup

  1. customThe cooled reaction mixture
  2. additionis poured onto ice
  3. extractionextracted with methylene chloride
  4. dry with materialBy drying over sodium sulphate
  5. customevaporating the organic phase, 8.9 g (98.4% of theory) of crude product
  6. customare obtained which
  7. customare recrystallised in ethanol

Sources & evidence

ORD record
ord-0c6e300621bf480f83dd461eb975ab9a
Source dataset
uspto-grants-1979_06
Patent number
US04157399

Linked notes

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