2-Chloro-5-nitropyridine → 2-(Ethylthio)-5-nitropyridine

HRID 2387286Notes

Reaction equation

HRID 2387286 reaction equation
[CH2:1]([S-:3])[CH3:2].[Na+].[N+:5]([C:8]1[CH:9]=[CH:10][C:11](Cl)=[N:12][CH:13]=1)([O-:7])=[O:6]>C1COCC1.O>[CH2:1]([S:3][C:11]1[CH:10]=[CH:9][C:8]([N+:5]([O-:7])=[O:6])=[CH:13][N:12]=1)[CH3:2]

Participants

5

Reactant 2

HCID 783082-Chloro-5-nitropyridineHCID 4459711Sodium ethanethiolate

Product 1

HCID 107975712-(Ethylthio)-5-nitropyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of sodium ethanethiolate (15.9 g; 0.189 mol) in 250 mL of THF and 100 mL of water at 0° C.-5° C. was added 5-nitro-2-chloropyridine (25.0 g; 0.158 mol). After 2 hours, the mixture was poured into 1200 mL of ice water, stirred for 15 minutes, and filtered. The solid was washed with water and dried in vacuo to provide 2-ethylsulfanyl-5-nitropyridine which was used without additional purification (28.1 g; 96%).

Workup

  1. filtrationfiltered
  2. washThe solid was washed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-69e4db151592428284fb2cc267c62950
Source dataset
uspto-grants-2012_09
Patent number
US08268859B2

Reaction notes

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