Cyanamide → HCID 178508192, compound

HRID 1993995Notes

Reaction equation

HRID 1993995 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=O.[N:12]#[C:13][NH2:14]>C(O)(=O)C.Cl>[NH2:14][C:13]1[N:12]=[N+:9]([O-:11])[C:3]2[CH:4]=[C:5]([OH:8])[CH:6]=[CH:7][C:2]=2[N:1]=1

Participants

5

Reactant 2

HCID 9864CyanamideHCID 37588824-Amino-3-Nitrophenol

Product 1

HCID 178508192HCID 178508192, compoundYield 51.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

7.7 g (0.05 mol) of 4-amino-3-nitrophenol was dissolved in 20 mL of glacial acetic acid and the resulting bright-red solution was heated to approximately 100° C. in 500 mL round-bottom flask equipped with a long condenser. To this solution was added a solution of 16.81 g (8.0 equivalent, 0.4 mol) of cyanamide in 20 mL of concentrated hydrochloric acid. In approximately 5-10 min the reaction mixture started to boil vigorously, so the heating was removed and it was stirred without heating until boiling subsided. Then the heating was reapplied and the reaction mixture was refluxed for 48 hrs. Then 150 mL of 30% NaOH was added and the resulting dark-reddish solution was refluxed for additional 3 hrs. Then it was cooled down to room temperature and dark-red slurry was formed. The red precipitate was filtered, re-dissolved in 200 mL of water and 1N HCl was added in portions with stirring until pH reached 5-4. The solution changed color from dark-red into light-yellow and a light-yellow fine precipitate was formed. The precipitate was filtered, washed twice with 50 mL of water, twice with 50 mL of acetonitrile and finally twice with 50 mL of diethyl ether and dried in vacuum to give 4.6 g of a bright-yellow solid. Yield: 51.7%.

Workup

  1. customequipped with a long condenser
  2. customwas removed
  3. temperaturewithout heating
  4. temperaturethe reaction mixture was refluxed for 48 hrs
  5. additionThen 150 mL of 30% NaOH was added
  6. temperaturethe resulting dark-reddish solution was refluxed for additional 3 hrs
  7. temperatureThen it was cooled down to room temperature
  8. customdark-red slurry was formed
  9. filtrationThe red precipitate was filtered
  10. dissolutionre-dissolved in 200 mL of water
  11. addition1N HCl was added in portions
  12. stirringwith stirring until pH
  13. customwas formed
  14. filtrationThe precipitate was filtered
  15. washwashed twice with 50 mL of water, twice with 50 mL of acetonitrile and finally twice with 50 mL of diethyl ether
  16. customdried in vacuum

Sources & evidence

ORD record
ord-589eeff059fd49b9a1e3d5b05c862bc9
Source dataset
uspto-grants-2010_01
Patent number
US07652051B2

Reaction notes

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