Water → HCID 501219, compound

HRID 2300997Notes

Reaction equation

HRID 2300997 reaction equation
[OH-].[K+].O.Cl[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][N+:6]=1[O-:12].[CH2:13]([SH:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([S:20][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N+:6]([O-:12])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7509Benzyl mercaptanHCID 14797Potassium HydroxideHCID 113326572,5-Dichloro-pyridine 1-oxide

Product 1

HCID 501219HCID 501219, compoundYield 59.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution consisting of 1.1 g (0.016 mole) of 85% KOH pellets, 50 ml of ethanol, and 0.5 ml of water was prepared. To this solution was added slowly, with stirring at room temperature, a mixture of 3.3 g (0.02 mole) of 2,5-dichloropyridine-N-oxide and 2.5 g (0.02 mole) of benzylmercaptan dissolved in 25 ml of ethanol. The reaction mixture was heated to about 60° C. for 2 hours and then evaporated to dryness. The residue was taken up in water and chloroform, the phases separated and the chloroform phase was dried over Na2SO4. The Na2SO4 was filtered off and the chloroform evaporated to leave a solid. The solid was recrystallized from ethanol to give 3.0 g of material, having a melting point of 130-133° C. Recovery was 2.2 g. The structure was confirmed by its IR spectrum.

Workup

  1. customwas prepared
  2. additionTo this solution was added slowly
  3. temperatureThe reaction mixture was heated to about 60° C. for 2 hours
  4. customevaporated to dryness
  5. customchloroform, the phases separated
  6. dry with materialthe chloroform phase was dried over Na2SO4
  7. filtrationThe Na2SO4 was filtered off
  8. customthe chloroform evaporated
  9. customto leave a solid
  10. customThe solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-a1c628fe83724f98ab776fefaf273046
Source dataset
uspto-grants-2002_12
Patent number
US06498254B1

Reaction notes

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