2-Furanmethanethiol → 4-((Furan-2-ylmethyl)thio)butanenitrile

HRID 1382766Notes

Reaction equation

HRID 1382766 reaction equation
[OH-].[Na+].[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH2:8][SH:9].Cl[CH2:11][CH2:12][CH2:13][C:14]#[N:15]>O.C(O)C>[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH2:8][S:9][CH2:11][CH2:12][CH2:13][C:14]#[N:15]

Participants

6

Reactant 3

HCID 73632-FuranmethanethiolHCID 123364-ChlorobutyronitrileHCID 14798Sodium Hydroxide

Product 1

HCID 212732874-((Furan-2-ylmethyl)thio)butanenitrileYield 94.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of sodium hydroxide (12.7 g) in water (50 ml) and ethanol (50 ml) was added dropwise over 30 minutes to a solution of furanylmethyl mercaptan (34.25 g) and 4-chlorobutyronitrile (31.58 g) in ethanol (150 ml) under nitrogen at 10° C. (ice-bath). The temperature rose slightly (to 18° C.) and the solution went cloudy. It was stirred at room temperature for 6.5 hours and allowed to stand for 20 hours. Ethanol was removed by evaporation at reduced pressure. The residue was dissolved in water (100 ml) and the solution was extracted with chloroform . The combined extracts were washed with water, dried (MgSO4) and chloroform evaporated at reduced pressure. The residual light-brown liquid was vacuum-distilled to give 4-(2-furanylmethylthio)butyronitrile (51.16 g), b.p.0.05 mm 112°-5° C.

Workup

  1. custom(to 18° C.)
  2. waitto stand for 20 hours
  3. customEthanol was removed by evaporation at reduced pressure
  4. dissolutionThe residue was dissolved in water (100 ml)
  5. extractionthe solution was extracted with chloroform
  6. washThe combined extracts were washed with water
  7. dry with materialdried (MgSO4) and chloroform
  8. customevaporated at reduced pressure
  9. distillationThe residual light-brown liquid was vacuum-distilled

Sources & evidence

ORD record
ord-8f1bcfeab7f34c849acc3a624dd88f59
Source dataset
uspto-grants-1989_02
Patent number
US04808589

Reaction notes

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