Hydrochloric Acid → HCID 178479526, compound

HRID 746036Notes

Reaction equation

HRID 746036 reaction equation
C(=O)(O)O.[NH2:5][NH:6][C:7]([NH2:9])=[NH:8].Cl.[Cl:11][C:12]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][CH:17]=[C:16]([Cl:23])[C:13]=1[CH:14]=O>O.C(O)C>[ClH:11].[Cl:11][C:12]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][CH:17]=[C:16]([Cl:23])[C:13]=1[CH:14]=[N:5][NH:6][C:7]([NH2:9])=[NH:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 27949122,6-Dichloro-3-nitrobenzaldehydeHCID 178513185HCID 178513185, compound

Product 1

HCID 178479526HCID 178479526, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Aminoguanidine hydrogen carbonate (1.24 g, 9.1 mmol) was added to a solution of concentrated hydrochloric acid (0.8 cm3, 9.3 mmol) in water (3 cm3). After diluting the resulting solution with ethanol (20 cm3), 2,6-dichloro-3-nitrobenzaldehyde (2.0 g, 9.1 mmol) was added and the mixture heated under reflux for 7 h. The solution was evaporated under reduced pressure and the residual solid suspended in refluxing ethanol, basified (pH 11) by addition of dilute sodium hydroxide solution and cooled to yield a white solid which was collected. This solid was dissolved in hot methanol and the solution acidified (pH 2) with ethanolic hydrogen chloride, diluted with diethyl ether and cooled to yield (2,6-dichloro-3-nitrobenzylideneamino)-guanidine hydrochloride as a white solid, m.p. 186°-7° C.

Workup

  1. additionwas added
  2. temperaturethe mixture heated
  3. temperatureunder reflux for 7 h
  4. customThe solution was evaporated under reduced pressure
  5. temperaturein refluxing ethanol
  6. additionby addition of dilute sodium hydroxide solution
  7. temperaturecooled
  8. customto yield a white solid which
  9. customwas collected
  10. dissolutionThis solid was dissolved in hot methanol
  11. additiondiluted with diethyl ether
  12. temperaturecooled

Sources & evidence

ORD record
ord-65cb7e0178344999b0b2991617e698d7
Source dataset
uspto-grants-1986_07
Patent number
US04602041

Reaction notes

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