Pyridine → S-Cyanomethyl 2-Thiofuroate

HRID 1414017Notes

Reaction equation

HRID 1414017 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].N1C=CC=CC=1.[SH:15][CH2:16][C:17]#[N:18]>CCOCC>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([S:15][CH2:16][C:17]#[N:18])=[O:7]

Participants

5

Reactant 3

HCID 1049PyridineHCID 682422-Furancarbonyl chlorideHCID 4346655Mercaptoacetonitrile

Product 1

HCID 12898756S-Cyanomethyl 2-ThiofuroateYield 64.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To an ice cold solution of furoyl chloride (4.0 ml; 0.04 mol) in ether (100 ml) is added dropwise a freshly prepared solution of pyridine (3.24 ml; 0.04 mol) in 1 N mercaptoacetonitrile (40 ml; 0.04 mol). After the addition is completed, the mixture is allowed to stir at room temperature overnight. The reaction mixture is then washed with water, saturated sodium bicarbonate solution, saturated brine, dried over sodium sulfate, and is concentrated in vacuo. The residue (6.0 g) is filtered through a 25 g column of silica gel and eluted with methylene chloride. The methylene chloride eluent is diluted with hexane, cooled and filtered to yield 4.3 g (64%) of title product, an orange solid, melting point 76°-78° C. Recrystallization from methylene chloride-hexane affords 3.7 g product, as a pale orange solid, melting point 77°-78° C.

Workup

  1. additionAfter the addition
  2. washThe reaction mixture is then washed with water, saturated sodium bicarbonate solution, saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationis concentrated in vacuo
  5. filtrationThe residue (6.0 g) is filtered through a 25 g column of silica gel
  6. washeluted with methylene chloride
  7. additionThe methylene chloride eluent is diluted with hexane
  8. temperaturecooled
  9. filtrationfiltered

Sources & evidence

ORD record
ord-b51631fbc9c24671bba5a865bb915eb4
Source dataset
uspto-grants-1981_02
Patent number
US04252814

Reaction notes

Loading…