Dimethylformamide dimethyl acetal → 1-(2'6'-Diethylphenyl)-4-methylamino-1,2-dihydro-1,3,5-triazin-2-one hydrochloride

HRID 1154858Notes

Reaction equation

HRID 1154858 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[NH:11][C:12]([NH:14][C:15](=[NH:18])[NH:16][CH3:17])=[O:13])[CH3:2].[CH3:19]N(C(OC)OC)C.[ClH:27].CO>CC#N>[ClH:27].[CH2:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH2:1][CH3:2])[C:4]=1[N:11]1[CH:17]=[N:16][C:15]([NH:18][CH3:19])=[N:14][C:12]1=[O:13])[CH3:10]

Participants

5

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 21893726Hydrochloride methanolHCID 178436233HCID 178436233, compound

Product 1

HCID 204574321-(2'6'-Diethylphenyl)-4-methylamino-1,2-dihydro-1,3,5-triazin-2-one hydrochlorideYield 47%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 22.8 g (80.0 mmol) of 1-(2,6-diethylphenyl)-3-methylamidinourea in CH3CN (100 ml) were added 19.1 g (160.0 mmol) of DMF-DMA and the reaction mixture was heated at reflux for 3 hours. The CH3CN was removed under reduced pressure and the residue partitioned between CHCl3 and H2O. The layers were separated and the aqueous layer extracted with CHCl3 (1×100 ml), dried (MgSO4) and concentrated under reduced pressure to give an off-white solid, which by NMR confirmed the desired free base. The solution was dissolved in H2OH and acidified with HCl/MeOH and the MeOH removed under reduced pressure to give an off-white solid which was crystallized from CH3CN to give after vacuum drying the weekend (105° C., house vacuum) 16.7 g (71%) of crude product. The material was recrystallized from CH3CN (a hot filtration was necessary to remove some undissolved solid) to give 11.0 g (47%) of desired product as a white crystalline solid:

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 3 hours
  3. customThe CH3CN was removed under reduced pressure
  4. customthe residue partitioned between CHCl3 and H2O
  5. customThe layers were separated
  6. extractionthe aqueous layer extracted with CHCl3 (1×100 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated under reduced pressure
  9. customto give an off-white solid, which by NMR
  10. dissolutionThe solution was dissolved in H2OH
  11. customthe MeOH removed under reduced pressure
  12. customto give an off-white solid which
  13. customwas crystallized from CH3CN
  14. customto give after vacuum
  15. dry with materialdrying the weekend (105° C., house vacuum) 16.7 g (71%) of crude product
  16. customThe material was recrystallized from CH3CN (
  17. filtrationa hot filtration
  18. customto remove some undissolved solid)

Sources & evidence

ORD record
ord-78aa37f587da465e91a963260ca39d71
Source dataset
uspto-grants-1981_11
Patent number
US04298608

Reaction notes

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