2,3-Diaminopyridine → 2-Furoyl isothiocyanate

HRID 1974313Notes

Reaction equation

HRID 1974313 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].[S-:9][C:10]#[N:11].[K+].NC1C(N)=CC=CN=1>CC(C)=O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([N:11]=[C:10]=[S:9])=[O:7]

Participants

5

Reactant 3

HCID 99562,3-DiaminopyridineHCID 682422-Furancarbonyl chlorideHCID 516872Potassium thiocyanate

Product 1

HCID 27592432-Furoyl isothiocyanate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
10 °C

Procedure

2-Furoylisothiocyanate is prepared from 2-furoyl chloride (13 g., 0.1 moles) and potassium thiocyanate (9.7 g., 0.1 moles) in acetone (35 ml.). The mixture is stirred at 10° C. for 15 minutes. 2,3-Diaminopyridine (2.8 g., 0.0257 moles) is added as a solid, the mixture stirred at 10° C. and allowed to warm to room temperature for three hours. The yellow solid is filtered, washed with acetone, slurried in 500 ml. water, filtered, washed with water and air dried. The product, 8.45 g. (80%) is purified by recrystallization from acetone giving 6.1 g. (57%) of desired product, as yellow crystals, m.p. 174° C. dec., of 2,3-bis[3-(2-furoyl)-2-thioureido]pyridine.

Workup

  1. stirringthe mixture stirred at 10° C.
  2. temperatureto warm to room temperature for three hours
  3. filtrationThe yellow solid is filtered
  4. washwashed with acetone
  5. filtrationwater, filtered
  6. washwashed with water and air
  7. customdried
  8. custom(80%) is purified by recrystallization from acetone giving 6.1 g

Sources & evidence

ORD record
ord-4ff81dce55a94d65bc898fc0d2eb33f9
Source dataset
uspto-grants-1976_12
Patent number
US04000285

Reaction notes

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