Hydrochloric Acid → HCID 178507226, compound

HRID 544408Notes

Reaction equation

HRID 544408 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[C:5]([Br:12])[C:4]=1[N:13]=[C:14]1[NH:18][CH2:17][CH2:16][NH:15]1>C(O)C.[Fe]>[NH2:9][C:7]1[CH:6]=[C:5]([Br:12])[C:4]([N:13]=[C:14]2[NH:18][CH2:17][CH2:16][NH:15]2)=[C:3]([Br:2])[CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178526429HCID 178526429, compound

Product 1

HCID 178507226HCID 178507226, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent2×

Procedure

A solution of concentrated hydrochloric acid (2.8 ml, 0.028 M) in aqueous ethanol (50%, 15 ml) was added dropwise to a stirred heated mixture of 2-(2,6-dibromo-4-nitro phenylimino)imidazolidine (4 g, 0.011 M) and iron powder (1.9 g, 0.034 M) in aqueous ethanol (50%). The mixture was heated under reflux for 3 hours after which time it was filtered hot and evaporated to a low volume. This residual solution was acidified with dilute hydrochloric acid and the resulting solid was removed. The solutionwas then basified with dilute aqueous sodium hydroxide yielding a solid which was collected. This solid was triturated with hot methanol which wasthen evaporated to leave a brown solid (3.2 g). This solid was chromatographed on alumina and eluted with a methanol in methylene chloride gradient. The fractions containing the required compound were combined and evaporated affording 2-(4-amino-2,6-dibromophenylimino)imidazoline dihydrochloride, mp>320° C. (1.6 g).

Workup

  1. temperatureheated
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 3 hours after which time it
  4. filtrationwas filtered hot
  5. customevaporated to a low volume
  6. customthe resulting solid was removed
  7. customwas collected
  8. customThis solid was triturated with hot methanol which
  9. customwasthen evaporated

Sources & evidence

ORD record
ord-4c18d10fdeca402a8d26d6a4a84163b2
Source dataset
uspto-grants-1984_05
Patent number
US04450170

Reaction notes

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