6-Chloro-3-nitropyridin-2-ylamine → 2-Amino-3-nitro-6-(phenylmercapto)pyridine

HRID 2289498Notes

Reaction equation

HRID 2289498 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4](Cl)[N:3]=1.[C:12]1([S-:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Na+]>CC(O)C.O>[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([S:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]=1

Participants

5

Reactant 2

HCID 27240356-Chloro-3-nitropyridin-2-ylamineHCID 4110039Sodium benzenethiolate

Product 1

HCID 110212152-Amino-3-nitro-6-(phenylmercapto)pyridineYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

2-amino-3-nitro-6-(phenylmercapto)pyridine was prepared by heating 2-amino-6-chloro-3-nitropyridine (84.0 g, 0.484 mol) and sodium thiophenolate (Fluka) (72.0 g, 0.545 mol) in 2-propanol (1500 mL) under reflux for 2 hours. After cooling to room temperature the suspension was diluted with water (100 ml), the solid was collected by vacuum filtration, washed with water and 2-propanol, and dried at 50° C. under vacuum to give 109.1 g (95% yield) of 2-amino-3-nitro-6-(phenylmercapto)pyridine, m.p. 148-152° C.).

Workup

  1. custom2-amino-3-nitro-6-(phenylmercapto)pyridine was prepared
  2. temperatureunder reflux for 2 hours
  3. filtrationthe solid was collected by vacuum filtration
  4. washwashed with water and 2-propanol
  5. customdried at 50° C. under vacuum

Sources & evidence

ORD record
ord-57f8f4c2f4b64906993302045729fd39
Source dataset
uspto-grants-2000_07
Patent number
US06093728

Reaction notes

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