2,3-Diaminopyridine → 2-Furoyl isothiocyanate

HRID 1657579Notes

Reaction equation

HRID 1657579 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 3 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 3 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-740db7121ce54bdb99dffd151cb879a2
Source dataset
uspto-grants-1976_06
Patent number
US03961063

Reaction notes

Loading…