Benzene → N-allyl-2-methoxy-2-(2-pyridyl)thioacetamide

HRID 1605677Notes

Reaction equation

HRID 1605677 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.C1C=CC=CC=1.C1([Li])C=CC=CC=1.[CH2:23]([N:26]=[C:27]=[S:28])[CH:24]=[CH2:25]>O>[CH2:23]([NH:26][C:27](=[S:28])[CH:3]([O:2][CH3:1])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)[CH:24]=[CH2:25]

Participants

6

Reactant 4

HCID 241Benzene3×HCID 5971Allyl IsothiocyanateHCID 2532202-(Methoxymethyl)pyridineHCID 178506676HCID 178506676, compound

Product 1

HCID 15581963N-allyl-2-methoxy-2-(2-pyridyl)thioacetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 9.95 g. (0.081 mole) of 2-(methoxymethyl)pyridine in 80 ml. of dry benzene is added dropwise to a chilled solution of 40 ml. (0.084 mole) of phenyl lithium in 80 ml. of dry benzene. The mixture is stirred at 0°C. for 1 hour after the addition is complete. Then 8.02 g. of allyl isothiocyanate in 50 ml. of benzene is added dropwise and the mixture is allowed to come to room temperature gradually. The mixture is then diluted with 500 ml. of water and acidified with 10% hydrochloric fractions The layers are separated and the organic layer is washed several times with water. The aqueous layers are combined, neutralized with 10% aqueous sodium hydroxide solution and then brought to pH 9 5% aqueous sodium bicarbonate solution, then extracted with chloroform. The chloroform extracts are washed once with brine and dried over magnesium sulfate. The solvent is removed and the residue is chromatographed on a silica gel column, eluting with ethyl acetate. The fraction, containing the product are combined and evaporated and the residue is recrystallized from ethyl acetate/hexane to give N-allyl-2-methoxy-2-(2-pyridyl)thioacetamide, m.p. 59.5°-60°C.

Workup

  1. additionafter the addition
  2. customto come to room temperature
  3. additionThe mixture is then diluted with 500 ml
  4. customare separated
  5. washthe organic layer is washed several times with water
  6. extractionextracted with chloroform
  7. washThe chloroform extracts are washed once with brine
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent is removed
  10. customthe residue is chromatographed on a silica gel column
  11. washeluting with ethyl acetate
  12. additionThe fraction, containing the product
  13. customevaporated
  14. customthe residue is recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-f076b89344c0447095c618fe501e0c97
Source dataset
uspto-grants-1976_04
Patent number
US03950522

Reaction notes

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