HCID 20552683, compound → 2-(Isothiocyanatomethyl)furan

HRID 2286522Notes

Reaction equation

HRID 2286522 reaction equation
[O-]Cl.[Na+].[CH2:4]([NH:10][C:11](=S)[S-:12])[C:5]1[O:9][CH:8]=[CH:7][CH:6]=1.[NH4+]>C(Cl)Cl>[CH2:4]([N:10]=[C:11]=[S:12])[C:5]1[O:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 20552683HCID 20552683, compoundHCID 23665760Sodium Hypochlorite

Product 1

HCID 783802-(Isothiocyanatomethyl)furanYield 81.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A 5.25% aqueous NaOCl solution (60 ml) is added to a stirred, cooled suspension of 1.9 g of ammonium furfuryldithiocarbamate in 20 ml of CH2Cl2 at such a rate that the temperature does not exceed 6° C. The mixture is stirred one hour at 20° C. and extracted with 3×50 ml of CH2Cl2. The combined extracts are washed with H2O (2×50 ml) dried (Na2SO2) and evaporated to afford 1.13 g of (81.2% yield) of crude furfurylisothiocyanate (NMR, IR are supportive of the structure).

Workup

  1. temperaturecooled
  2. customdoes not exceed 6° C
  3. extractionextracted with 3×50 ml of CH2Cl2
  4. washThe combined extracts are washed with H2O (2×50 ml)
  5. dry with materialdried (Na2SO2)
  6. customevaporated

Sources & evidence

ORD record
ord-7d389c4843a0449f981edecedbc0c4cb
Source dataset
uspto-grants-1981_05
Patent number
US04267191

Reaction notes

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