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

HRID 28055Notes

Reaction equation

HRID 28055 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>[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

5

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 1

HCID 6342AcetonitrileSolvent

Procedure

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

Workup

  1. additionTo a suspension of 22.8 g
  2. temperatureat reflux for 3 hours
  3. customThe CH3CN is removed under reduced pressure
  4. customthe residue partitioned between CHCl3 and H2O
  5. customThe layers are separated
  6. extractionthe aqueous layer extracted with CHCl3 (1×100)
  7. washThe combined CHCl3 extracts are 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. dissolutionThe solution is dissolved in H2OH
  12. customthe MeOH removed under reduced pressure
  13. customto give an off-white solid which
  14. customis crystallized from CH3CN
  15. customto give after vacuum
  16. customdrying over the weekend (105° C., house vacuum) 16.7 g
  17. customThe material is recrystallized from CH3CN (
  18. filtrationa hot filtration
  19. customto remove some undissolved solid)
  20. customto give 11.0 g

Sources & evidence

ORD record
ord-e5ac94d0329e4f9591a29f1a682f5b81
Source dataset
uspto-grants-1980_09
Patent number
US04225315

Reaction notes

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