Thiophenol → 5-(Phenylsulfanyl)pyridin-2-amine

HRID 1447598Notes

Reaction equation

HRID 1447598 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][N:3]=1.[C:9]1([SH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C[O-].[Na+]>[Cu].CO>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:15][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 885792-Pyridinamine, 5-iodo-HCID 10942334Sodium Methoxide

Product 1

HCID 124108405-(Phenylsulfanyl)pyridin-2-amineYield 64.3%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 887MethanolSolvent

Procedure

11 G. (0.05 moles) of 2-amino 5-iodo pyridine, 7.2 ml. (0.07 moles) of thiophenol, 3.8 g. (0.07 moles) of sodium methoxide, 1.0 g of copper powder and 100 ml. of methanol are heated 150° C. for 12 hours in a glass lined bomb. The reaction mixture is concentrated to dryness, extracted with chloroform and the chloroform extracts concentrated to dryness in vacuo affording 15 g. of a crude product which is chromatographed on 600 g. of silica gel, eluting with methylene chloride and ethyl acetate-methylene chloride 50% mixture affording 6.5 g of 2-amino 5-phenylthio pyridine, m.p. 127° to 129° C.

Workup

  1. concentrationThe reaction mixture is concentrated to dryness
  2. extractionextracted with chloroform
  3. concentrationthe chloroform extracts concentrated to dryness in vacuo
  4. customaffording 15 g
  5. customof a crude product which is chromatographed on 600 g
  6. washof silica gel, eluting with methylene chloride and ethyl acetate-methylene chloride 50% mixture

Sources & evidence

ORD record
ord-fcc01d6ac21c4d659996548c334ccbd2
Source dataset
uspto-grants-1979_12
Patent number
US04177274

Reaction notes

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