Dimethyl Sulfoxide → 4-Benzylidene amino-1-(4-benzyloxy-3,5-dimethylbenzyl)-5-imidazole carboxamide

HRID 382387Notes

Reaction equation

HRID 382387 reaction equation
CS(C)=O.[CH2:5]([O:12][C:13]1[C:20]([CH3:21])=[CH:19][C:16]([CH2:17]O)=[CH:15][C:14]=1[CH3:22])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH:23](=[N:30][C:31]1[N:32]=[CH:33][NH:34][C:35]=1[C:36]([NH2:38])=[O:37])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>Cl[Si](C)(C)C.CN(C)C=O.O>[CH:23](=[N:30][C:31]1[N:32]=[CH:33][N:34]([CH2:17][C:16]2[CH:19]=[C:20]([CH3:21])[C:13]([O:12][CH2:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)=[C:14]([CH3:22])[CH:15]=2)[C:35]=1[C:36]([NH2:38])=[O:37])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 43118033[4-(Benzyloxy)-3,5-dimethylphenyl]methanolHCID 539704464-Benzylideneamino-5-imidazolecarboxamide

Product 1

HCID 569904764-Benzylidene amino-1-(4-benzyloxy-3,5-dimethylbenzyl)-5-imidazole carboxamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6397ChlorotrimethylsilaneSolvent

Procedure

0.48 ml of dimethylsulfoxide was added to a solution of 1.49 g (6.15 mmol) of 4-benzyloxy-3,5-dimethylbenzyl alcohol in 40 ml of chlorotrimethylsilane, and the mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated under vacuum. The concentrate was dissolved in ethyl acetate, washed with distilled water and saturation brine, and dried over anhydrous magnesium sulfate. The residue obtained by concentrating the dry product under vacuum was dissolved in 30 ml of N,N-dimethylformamide. This solution was mixed with a suspension of 0.88 g (4.1 mmol) of 4-benzylideneamino-5-imidazolecarboxamide and 2.27 g (16.4 mmol) of potassium carbonate in 30 ml of N,N-dimethylformamide. After the addition of 1.64 ml of distilled water, the mixture was heated for 10 minutes and stirred overnight. The reaction solution was concentrated under vacuum and distilled water was added to the concentrate to precipitate a crude product. The precipitate was collected by filtration using a funnel glass filter. The solid obtained was washed with distilled water and toluene, and dried under vacuum to obtain 4-benzylidene amino-1-(4-benzyloxy-3,5-dimethylbenzyl)-5-imidazole carboxamide. The resulting compound was suspended in 25 ml of 1,4-dioxane and 25 ml of 1N aqueous solution of hydrochloric acid was added, followed by stirring overnight. The reaction solution was washed with ether, added 25 ml of methanol, and neutralized with 4N aqueous solution of sodium hydroxide. The organic solvent was evaporated under vacuum and the residue was allowed to stand overnight in a refrigerator. The precipitated solid was collected by filtration, washed with distilled water, and dried to obtain 1.10 g of 4-amino-1-(4-benzyloxy-3,5-dimethylbenzyl)-5-imidazole carboxamide (yield 86%).

Workup

  1. concentrationThe reaction solution was concentrated under vacuum
  2. dissolutionThe concentrate was dissolved in ethyl acetate
  3. washwashed with distilled water and saturation brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe residue obtained
  6. concentrationby concentrating the dry product under vacuum
  7. dissolutionwas dissolved in 30 ml of N,N-dimethylformamide
  8. temperaturethe mixture was heated for 10 minutes
  9. stirringstirred overnight
  10. concentrationThe reaction solution was concentrated under vacuum
  11. distillationdistilled water
  12. additionwas added to the
  13. concentrationconcentrate
  14. customto precipitate a crude product
  15. filtrationThe precipitate was collected by filtration
  16. filtrationfilter
  17. customThe solid obtained
  18. washwas washed with distilled water and toluene
  19. customdried under vacuum

Sources & evidence

ORD record
ord-fe8e8c1ce121426cb2fa7efa4eb60536
Source dataset
uspto-grants-2001_10
Patent number
US06310070B1

Reaction notes

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