p-Chlorothiophenol → 5-[(4-Chlorophenyl)sulfanyl]pyridin-2-amine

HRID 444472Notes

Reaction equation

HRID 444472 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([SH:16])=[CH:12][CH:11]=1.C[O-].[Na+]>[Cu].CO>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:16][C:13]2[CH:14]=[CH:15][C:10]([Cl:9])=[CH:11][CH:12]=2)=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 7815p-ChlorothiophenolHCID 706222-Amino-5-bromopyridineHCID 10942334Sodium Methoxide

Product 1

HCID 129127435-[(4-Chlorophenyl)sulfanyl]pyridin-2-amine

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 887MethanolSolvent

Procedure

2-Amino-5-bromopyridine (7.8 grams), 4-chlorothiophenol (9.2 grams), sodium methoxide (3.5 grams), and copper powder (1.0 gram) were reacted in 100 ml. of methanol, for 12 hours, in a bomb, in accordance with the procedures of J. Med. Chem. 21, 235 (1978). The reaction mixture was filtered, washed with methanol, and methanol removed by evaporation. The methanol washes were combined with ethyl acetate extracts of solids made after refluxing on a steam bath for one hour. Solvents were removed and the solids dissolved in ethyl acetate and filtered to remove insolubles. The liquid was passed over a silica column with ethyl acetate, and the fraction corresponding to the product amine (Rf ≅0.2) collected., yield 6.5 grams, m.p., 161°-163° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with methanol, and methanol
  3. customremoved by evaporation
  4. temperatureafter refluxing on a steam bath for one hour
  5. customSolvents were removed
  6. dissolutionthe solids dissolved in ethyl acetate
  7. filtrationfiltered
  8. customto remove insolubles
  9. customthe fraction corresponding to the product amine (Rf ≅0.2) collected
  10. customm.p., 161°-163° C.

Sources & evidence

ORD record
ord-5b40d5c1b2344b7d891aefd799c3405e
Source dataset
uspto-grants-1981_04
Patent number
US04264605

Reaction notes

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