Hydrochloric Acid → (1E)-1-[amino-(2,4,6-trichloroanilino)methylidene]-2-methylguanidine;hydrochloride

HRID 1973121Notes

Reaction equation

HRID 1973121 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[C:5]([Cl:10])[C:3]=1[NH2:4].[CH3:11][NH:12][C:13]([NH:15][C:16]#[N:17])=[NH:14].Cl>C(O)CCC>[ClH:1].[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[C:5]([Cl:10])[C:3]=1[NH:4][C:16]([NH:15][C:13]([NH:12][CH3:11])=[NH:14])=[NH:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 124712,4,6-TrichloroanilineHCID 178485119HCID 178485119, compound

Product 1

HCID 178485125(1E)-1-[amino-(2,4,6-trichloroanilino)methylidene]-2-methylguanidine;hydrochloride

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To 20 g (0.1 mole) of 2,4,6-trichloroaniline and 12.6 g (0.1 mole) of 1-methyl-3-cyanoguanidine in 10 ml (0.1 mole) of concentrated hydrochloric acid is added 125 ml of n-butanol. The reaction mixture is refluxed for 17 hours, cooled and the alcohol evaporated off. The residue is extracted with ether after making it alkaline with 40% sodium hydroxide. The ether extract is dried over potassium carbonate and evaporated. The residue is dissolved in methanol, the pH adjusted to about 7, charcoal filtered and evaporated. The residue is triturated with ether and the solid that forms is recrystallized from water to obtain 1-(2,4,6-trichlorophenyl)-5-methylbiguanide hydrochloride.

Workup

  1. temperatureThe reaction mixture is refluxed for 17 hours
  2. temperaturecooled
  3. customthe alcohol evaporated off
  4. extractionThe residue is extracted with ether
  5. extractionThe ether extract
  6. dry with materialis dried over potassium carbonate
  7. customevaporated
  8. dissolutionThe residue is dissolved in methanol
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue is triturated with ether
  12. customthe solid that forms is recrystallized from water

Sources & evidence

ORD record
ord-e5830e06368146c2b98d0d78dd43429d
Source dataset
uspto-grants-1976_12
Patent number
US03996232

Reaction notes

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