Hydrochloric Acid → HCID 178489039, compound

HRID 1595410Notes

Reaction equation

HRID 1595410 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[C:16]([CH3:23])[CH:15]=3)=[N:11][C:10]=2[C:24]([NH:26][C:27]2[S:28][CH:29]=[CH:30][N:31]=2)=[O:25])=[CH:5][CH:4]=1.[ClH:32].C(=O)([O-])O>C(O)C.O1CCOCC1.[Fe]>[ClH:32].[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]2[NH:13][C:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[C:10]([C:24]([NH:26][C:27]3[S:28][CH:29]=[CH:30][N:31]=3)=[O:25])[N:11]=2)=[CH:15][C:16]=1[CH3:23]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 769Bicarbonate IonHCID 178489045HCID 178489045, compound

Product 1

HCID 178489039HCID 178489039, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

5-(4-Methoxyphenyl)-2-(3-methyl-4-nitrophenyl)-N-(2-thiazolyl)imidazole-4-carboxamide (1.5 g) obtained in Example 84 was dissolved in 50% aqueous ethanol solution (60 ml) and dioxane (50 ml), and iron powder (0.6 g) was added. Conc. hydrochloric acid (0.06 ml) was added under refluxing and the mixture was refluxed for 1 hr. A saturated aqueous hydrogencarbonate solution was added and the mixture was neutralized. An insoluble matter was filtered off and the filtrate was concentrated under reduced pressure. Water was added to the residue and the mixture was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. After drying, the solvent was evaporated under reduced pressure. The obtained crystals (0.79 g) were dissolved in methanol (24 ml) and dioxane (35 ml) and 1 M hydrochloric acid—ether solution (5.85 ml) was added. The mixture was stirred at room temperature for 1 hr. The solvent was evaporated under reduced pressure and the obtained crystals were recrystallized from ethanol to give the objective 2-(4-amino-3-methylphenyl)-5-(4-methoxyphenyl)-N-(2-thiazolyl)imidazole-4-carboxamide. Hydrochloride (0.43 g): melting point 250° C. or above

Workup

  1. temperatureunder refluxing
  2. temperaturethe mixture was refluxed for 1 hr
  3. filtrationAn insoluble matter was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionWater was added to the residue
  6. extractionthe mixture was extracted with ethyl acetate
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customAfter drying
  9. customthe solvent was evaporated under reduced pressure
  10. dissolutionThe obtained crystals (0.79 g) were dissolved in methanol (24 ml)
  11. additiondioxane (35 ml) and 1 M hydrochloric acid—ether solution (5.85 ml) was added
  12. customThe solvent was evaporated under reduced pressure
  13. customthe obtained crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-0b1ea24eb5f5464490ab3871155ad642
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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