Furfurylamine → 2-(Isothiocyanatomethyl)furan

HRID 1446786Notes

Reaction equation

HRID 1446786 reaction equation
[CH2:1]([NH2:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C(Cl)Cl.[O-]Cl.[Na+].[C:16](=S)=[S:17]>O>[CH2:1]([N:7]=[C:16]=[S:17])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 3438FurfurylamineHCID 6344DichloromethaneHCID 6348Carbon DisulfideHCID 14798Sodium HydroxideHCID 23665760Sodium Hypochlorite

Product 1

HCID 783802-(Isothiocyanatomethyl)furan

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

Furfurylamine (9.71 g) is added over 30 minutes to a stirred, cooled mixture of 8.84 g of NaOH, 20 ml of CH2Cl2, 15 ml of H2O and 7.5 ml of CS2. The mixture is stirred 55 minutes in the ice bath and 600 ml of 5.25% aqueous NaOCl solution is added over 1 hour and 45 minutes (temperature is maintained at 8° C. or less). After stirring 16 hours at 20° C., the reaction mixture is extracted three times with CH2Cl2 (total volume of combined CH2Cl2 extracts is 600 ml). The CH2Cl2 extract is washed with 2×100 ml of H2O, dried with Na2SO4 and evaporated to give 12.4 g of crude furfurylisothiocyanate.

Workup

  1. temperaturecooled
  2. additionis added over 1 hour and 45 minutes
  3. temperature(temperature is maintained at 8° C. or less)
  4. extractionthe reaction mixture is extracted three times with CH2Cl2 (total volume of combined CH2Cl2 extracts is 600 ml)
  5. extractionThe CH2Cl2 extract
  6. washis washed with 2×100 ml of H2O
  7. dry with materialdried with Na2SO4
  8. customevaporated

Sources & evidence

ORD record
ord-17ced63a13d843799cdaee3ed5400c17
Source dataset
uspto-grants-1982_02
Patent number
US04313885

Reaction notes

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