Resorcinol → HCID 178514116, compound

HRID 436882Notes

Reaction equation

HRID 436882 reaction equation
[N:1]#[C:2]Cl.[C:4]1([CH:11]=[CH:10][CH:9]=[C:7]([OH:8])[CH:6]=1)[OH:5].C(N(CC)CC)C>C(O)(C)C>[O-:5][C:2]#[N:1].[C:4]1([CH:11]=[CH:10][CH:9]=[C:7]([OH:8])[CH:6]=1)[OH:5]

Participants

5

Reactant 3

HCID 5054ResorcinolHCID 8471TriethylamineHCID 10477Cyanogen Chloride

Product 1

HCID 178514116HCID 178514116, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

271 g (4.4 mols) of cyanogen chloride in 1.1 liter of isopropanol are introduced at -5° C. into a 3 liter glass vessel equipped with a stirrer, a thermometer and an inlet pipe. By means of a metering pump, a solution of 220 g (2 mols) of resorcinol and 430 g (4.04 mols) of triethyl amine in 750 ml of isopropanol is pumped in below the surface with stirring. The reaction temperature is best kept at -5° C. to +3° C. On completion of the reaction, the crystalline sludge formed is filtered off under suction from the isopropanol and the filter residue is washed with 100 ml of isopropanol. The residue is thoroughly stirred with 1.1 liter of water and filtered off under suction again. The filter residue is then taken up in 800 ml of methylene chloride and washed with water until free from chloride. Following the addition of 600 ml of perchloroethylene, the methylene chloride distils off initially at 45° to 50° C. and subsequently at 60° C. and at about 160 Torr. The residue is left to cool with stirring to 5°-10° C. and the resorcinol dicyanate which has crystallised out is filtered off under suction, washed twice with 50 ml of perchloroethylene and dried in a stream of air. 270 g (84% of the theoretical) of resorcinol cyanate are obtained. Mp: 81° C., nD90 :1.4980

Workup

  1. customequipped with a stirrer
  2. customis best kept at -5° C. to +3° C
  3. customOn completion of the reaction
  4. customthe crystalline sludge formed
  5. filtrationis filtered off under suction from the isopropanol
  6. washthe filter residue is washed with 100 ml of isopropanol
  7. stirringThe residue is thoroughly stirred with 1.1 liter of water
  8. filtrationfiltered off under suction again
  9. washwashed with water until free from chloride
  10. additionthe addition of 600 ml of perchloroethylene
  11. customthe methylene chloride distils off initially at 45° to 50° C. and subsequently at 60° C. and at about 160 Torr
  12. waitThe residue is left
  13. temperatureto cool
  14. stirringwith stirring to 5°-10° C.
  15. customthe resorcinol dicyanate which has crystallised out
  16. filtrationis filtered off under suction
  17. washwashed twice with 50 ml of perchloroethylene
  18. customdried in a stream of air

Sources & evidence

ORD record
ord-23f86a8d27d14887bd2a9674e42013e0
Source dataset
uspto-grants-1977_06
Patent number
US04028393

Reaction notes

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