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

HRID 1395429Notes

Reaction equation

HRID 1395429 reaction equation
[ClH:1].[CH2:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH3:11])[C:5]=1[NH:12][C:13]([NH:15][C:16](=[NH:19])[NH:17][CH3:18])=[O:14])[CH3:3].[CH3:20]N(C(OC)OC)C.Cl.CO>CC#N.O>[ClH:1].[CH2:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH2:2][CH3:3])[C:5]=1[N:12]1[CH:18]=[N:17][C:16]([NH:19][CH3:20])=[N:15][C:13]1=[O:14])[CH3:11]

Participants

6

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 21893726Hydrochloride methanolHCID 178436234HCID 178436234, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a suspension of 22.8 g (80.0 mmol) of 1-(2,6-diethylphenyl)-3-methylamidinourea hydrochloride 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). The combined CHCl3 extracts were washed with H2O (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 H2O 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 over 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)
  7. washThe combined CHCl3 extracts were washed with H2O (1×100 ml)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated under reduced pressure
  10. customto give an off-white solid, which by NMR
  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 over 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-9152fdf6dd634d78afe428e13c7f3d50
Source dataset
uspto-grants-1980_05
Patent number
US04203984

Reaction notes

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