Ethanol → 2-(Benzylthio)-3-nitropyridine

HRID 2300994Notes

Reaction equation

HRID 2300994 reaction equation
C(O)C.[OH-].[K+].[CH2:6]([SH:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl[C:15]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=[CH:17][N:16]=1>O>[CH2:6]([S:13][C:15]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=[CH:17][N:16]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 7509Benzyl mercaptanHCID 14797Potassium HydroxideHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 5073002-(Benzylthio)-3-nitropyridineYield 37.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

To a stirred solution of 35 ml of ethanol, 1 ml of water, and 2.0 g (0.025 mole) of 85% KOH pellets was added 3.2 g (0.025 mole) of benzyl mercaptan. To this mixture was added 4 g (0.025 mole) of 2-chloro-3-nitropyridine. After complete addition (20 minutes), the reaction mixture was warmed to 55° C. and held at that temperature for 25 minutes. It was then allowed to cool to room temperature over the next hour. The solid was filtered off (KCl) and the ethanol was removed from the filtrate. The residue was treated with 40 ml of acetone by warming, cooling and then filtering to remove more KCl. The filtrate was evaporated to leave an oil which solidified. The solid was recrystallized from 40 ml of ethanol to give 2.3 g of crystals, having a melting point of 57-59° C. The infrared spectrum was consistent with the structure. A second crop of 1.3 g of impure product was also obtained.

Workup

  1. additionAfter complete addition (20 minutes)
  2. temperatureto cool to room temperature over the next hour
  3. filtrationThe solid was filtered off (KCl)
  4. customthe ethanol was removed from the filtrate
  5. additionThe residue was treated with 40 ml of acetone
  6. temperatureby warming
  7. temperaturecooling
  8. filtrationfiltering
  9. customto remove more KCl
  10. customThe filtrate was evaporated
  11. customto leave an oil which
  12. customThe solid was recrystallized from 40 ml of ethanol

Sources & evidence

ORD record
ord-e4d3c287fc3c487fa3527bd906a6babd
Source dataset
uspto-grants-2002_12
Patent number
US06498254B1

Reaction notes

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