2-Chloro-3-nitropyridine → 2-Isothiocyanato-3-nitropyridine

HRID 1683310Notes

Reaction equation

HRID 1683310 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[N-:11]=[C:12]=[S:13].[K+]>C(O)(=O)C>[N:11]([C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1)=[C:12]=[S:13]

Participants

4

Reactant 2

HCID 796132-Chloro-3-nitropyridineHCID 10931372Isothiocyanatopotassium

Product 1

HCID 190433452-Isothiocyanato-3-nitropyridine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 10 g sample of 2-chloro-3-nitropyridine, an 8 g sample of potassium isothiocyanate, and 75 ml of acetic acid were combined and refluxed for 2 h. The reaction mixture was then cooled and poured into 400 ml of ice/H2O. The resulting solid was washed with water, redissolved in ethyl acetate and washed (4x) with water. The ethyl acetate solution was then treated with activated carbon, dried over anhydrous Na2SO4, filtered and evaporated to dryness to provide 3.72 g of the title compound. m.p.=115°-118° C.

Workup

  1. temperaturerefluxed for 2 h
  2. temperatureThe reaction mixture was then cooled
  3. washThe resulting solid was washed with water
  4. dissolutionredissolved in ethyl acetate
  5. washwashed (4x) with water
  6. additionThe ethyl acetate solution was then treated with activated carbon
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-599fcb0d50864e0d9e66df83ef4a6b63
Source dataset
uspto-grants-1997_06
Patent number
US05637693

Reaction notes

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