Hydrochloric Acid → HCID 20434624, compound

HRID 27193Notes

Reaction equation

HRID 27193 reaction equation
[CH3:1][NH:2][C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:4]=1Cl.[ClH:11].C1C(O)=CC=CC=1C.[N:20]#[C:21][NH2:22].[OH-].[Na+]>CCOCC>[ClH:9].[Cl:11][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([Cl:9])[C:3]=1[N:2]([CH3:1])[C:21]([NH2:22])=[NH:20]

Participants

7

Reactant 5

HCID 313Hydrochloric Acid2×HCID 342M-CresolHCID 9864CyanamideHCID 14798Sodium HydroxideHCID 146119262,6-Dichloro-N-methylaniline

Product 1

HCID 20434624HCID 20434624, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 55.4 g (0.315 mole) of N-methyl-2,6-dichloroaniline 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-dichlorophenyl)-1-methylguanidine hydrochloride.

Workup

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

Sources & evidence

ORD record
ord-524568bf38ce4974b03d5afbfa84b9a8
Source dataset
uspto-grants-1980_09
Patent number
US04220658

Reaction notes

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