Hydrochloric Acid → HCID 178485094, compound

HRID 2398828Notes

Reaction equation

HRID 2398828 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].Cl.C1C(O)=CC=CC=1C.[CH3:19][NH:20][C:21]#[N:22].[OH-].[Na+]>CCOCC>[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH:4][C:21]([NH:20][CH3:19])=[NH:22]

Participants

7

Reactant 5

HCID 313Hydrochloric Acid2×HCID 342M-CresolHCID 68962,6-DimethylanilineHCID 14798Sodium HydroxideHCID 119415Methylcyanamide

Product 1

HCID 178485094HCID 178485094, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 40.5 g. (0.315 mole) of 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 17.7 g. (0.315 mole) of methyl 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)-3-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-faabdfd61b5249a2821da2b03cc14b94
Source dataset
uspto-grants-1977_05
Patent number
US04025652

Reaction notes

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