Hydrochloric Acid → 1-(2,6-Dimethylphenyl)-1-methylguanidine

HRID 1764192Notes

Reaction equation

HRID 1764192 reaction equation
[CH3:1][NH:2][C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5]C=1C.Cl.C1C(O)=CC=CC=1C.[N:20]#[C:21][NH2:22].[OH-].[Na+].CCO[CH2:28][CH3:29]>>[CH3:9][C:8]1[CH:7]=[CH:6][CH:5]=[C:28]([CH3:29])[C:3]=1[N:2]([CH3:1])[C:21]([NH2:22])=[NH:20]

Participants

7

Reactant 6

HCID 313Hydrochloric Acid2×HCID 342M-CresolHCID 3283Diethyl EtherHCID 9864CyanamideHCID 14798Sodium HydroxideHCID 136604N,2,6-trimethylaniline

Product 1

HCID 204344741-(2,6-Dimethylphenyl)-1-methylguanidine

Procedure

To 40.5 g. (0.315 mole) of N-methyl-2,6-dimethylaniline is added 0.4 moles of ethereal HCl and 200 ml. of m-cresol. The mixture is then stirred and heated on a steam bath to drive off the ether and excess hydrogen chloride. To the resultant mixture is then added 13.3 g. (0.315 mole) of cyanamide then heated for 2 hours on a steam bath. The reaction mixture is then cooled, added to 150 ml. of conc. sodium hydroxide solution, cooled and extracted with 2 liters of ether. The ether layer is washed with 2 × 1 liter of water, dried over sodium sulfate, charcoaled and evaporated. The residue is triturated with hexane and the precipitate is filtered off and washed with ether and dried to obtain 1-(2,6-dimethylphenyl)-1-methylguanidine.

Workup

  1. temperatureheated on a steam bath
  2. temperatureThe reaction mixture is then cooled
  3. additionadded to 150 ml
  4. extractionextracted with 2 liters of ether
  5. washThe ether layer is washed with 2 × 1 liter of water
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe residue is triturated with hexane
  9. filtrationthe precipitate is filtered off
  10. washwashed with ether
  11. customdried

Sources & evidence

ORD record
ord-73b0e67fc908473eb330717c5f688239
Source dataset
uspto-grants-1978_09
Patent number
US04115564

Reaction notes

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