2-Aminothiophenol → 2-(2-Aminophenyl)sulfanylbenzonitrile

HRID 1609285Notes

Reaction equation

HRID 1609285 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].C(=O)([O-])[O-].[K+].[K+].Cl[C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[C:18]#[N:19]>CN(C=O)C>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[C:18]#[N:19]

Participants

5

Reactant 3

HCID 87132-AminothiophenolHCID 11430Potassium CarbonateHCID 133912-Chlorobenzonitrile

Product 1

HCID 3662332-(2-Aminophenyl)sulfanylbenzonitrileYield 84.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In 10 ml of DMF was dissolved 1.25 g of orthoaminothiophenol followed by addition of 1.38 g of potassium carbonate. The mixture was preheated at 100° C. and after 1.45 g of o-chlorobenzonitrile was added, the mixture was stirred in an argon gas stream at 100° C. for 1 hour. To the reaction mixture was added ice-water and the mixture was extracted with ethyl acetate. The extract was washed with water twice and dried over magnesium sulfate and the solvent was distilled off. The residue was crystallized from n-hexane-isopropyl ether to give 1.91 g of the title compound as white crystals, m.p. 88°-90° C.

Workup

  1. customwas preheated at 100° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water twice
  4. dry with materialdried over magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was crystallized from n-hexane-isopropyl ether

Sources & evidence

ORD record
ord-e4752e23f9ad422380fae808ae1345c7
Source dataset
uspto-grants-1995_03
Patent number
US05399703

Reaction notes

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