Hydrochloric Acid → (1E)-1-[amino-[3,5-bis(trifluoromethyl)anilino]methylidene]-2-methylguanidine

HRID 1973119Notes

Reaction equation

HRID 1973119 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[NH2:6].[CH3:16][NH:17][C:18]([NH:20][C:21]#[N:22])=[NH:19].Cl>O>[F:1][C:2]([F:14])([F:15])[C:3]1[CH:4]=[C:5]([NH:6][C:21]([NH:20][C:18]([NH:17][CH3:16])=[NH:19])=[NH:22])[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9480Benzenamine, 3,5-bis(trifluoromethyl)-HCID 178485119HCID 178485119, compound

Product 1

HCID 178485121(1E)-1-[amino-[3,5-bis(trifluoromethyl)anilino]methylidene]-2-methylguanidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 22.9 g (0.1 mole) of 3,5-di(trifluoromethyl)aniline and 12.6 g (0.1 mole) of 1-methyl-3-cyanoguanidine is added 10 ml of concentrated hydrochloric acid and 20 ml of water. The solution is heated on a steam bath for 1 hour at which time a solid precipitates out. The reaction mixture is cooled to room temperature, made strongly alkaline with 40% NaOH and extracted with ether. The ether layer is dried over potassium carbonate, and evaporated in vacuo to obtain an oil. The residue is triturated with 500 ml heptane and the solid which forms is recrystallized from methylene chloride to obtain 1-[3,5-di(trifluoromethyl)phenyl]-5-methylbiguanide.

Workup

  1. temperatureThe solution is heated on a steam bath for 1 hour at which time a solid
  2. customprecipitates out
  3. extractionextracted with ether
  4. dry with materialThe ether layer is dried over potassium carbonate
  5. customevaporated in vacuo
  6. customto obtain an oil
  7. customThe residue is triturated with 500 ml heptane
  8. customthe solid which forms is recrystallized from methylene chloride

Sources & evidence

ORD record
ord-524dabb30bdc4177a71c6df0513b5add
Source dataset
uspto-grants-1976_12
Patent number
US03996232

Reaction notes

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