Pyridine → 4-Nitrobenzyl thioacetate

HRID 726416Notes

Reaction equation

HRID 726416 reaction equation
[C:1]([OH:4])(=[S:3])[CH3:2].N1C=CC=CC=1.[N+:11]([C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][CH:15]=1)([O-:13])=[O:12]>O1CCCC1>[C:1]([O:4][CH2:18][C:17]1[CH:20]=[CH:21][C:14]([N+:11]([O-:13])=[O:12])=[CH:15][CH:16]=1)(=[S:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 74824-Nitrobenzyl chlorideHCID 178418634HCID 178418634, compound

Product 1

HCID 197105064-Nitrobenzyl thioacetateYield 77.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Thioacetic acid (20 cm3, 0.28 mol) and anhydrous pyridine (15.2 cm3, 0.188 mol) were added to a solution of 4-nitrobenzyl chloride (12.0 g, 70 mmol) in anhydrous tetrahydrofuran (200 cm3). The stirred reactants were heated at 50° C. for 24 h. The cooled products were filtered and the flltrate was evaporated under reduced pressure. The residue was dissolved in dichloromethane (300 cm3) and the resulting solution was washed with saturated aqueous sodium hydrogen carbonate (2×250 cm3), dried (MgSO4) and concentrated under reduced pressure. The residue was crystallized from ethyl acetate--petroleum ether (bp 60°-80° C.) to give 4-nitrobenzyl thioacetate 16a (11.43 g, 77%) as pale yellow needles, m.p. 55.5°-57.5° C.

Workup

  1. filtrationThe cooled products were filtered
  2. customthe flltrate was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane (300 cm3)
  4. washthe resulting solution was washed with saturated aqueous sodium hydrogen carbonate (2×250 cm3)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-53d19d5d9b7047188a8e138cc88dc7b2
Source dataset
uspto-grants-1998_01
Patent number
US05708161

Reaction notes

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