Water → HCID 178424019, compound

HRID 1595386Notes

Reaction equation

HRID 1595386 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=3)=[N:10][C:9]=2[C:22]([NH:24][C:25]2[S:26][CH:27]=[CH:28][N:29]=2)=[O:23])=[CH:4][CH:3]=1.[Sn](Cl)Cl.O.C(=O)([O-])[O-].[K+].[K+]>CO.Cl>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([C:11]2[NH:12][C:8]([C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=3)=[C:9]([C:22]([NH:24][C:25]3[S:26][CH:27]=[CH:28][N:29]=3)=[O:23])[N:10]=2)=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 24479Stannous ChlorideHCID 178424020HCID 178424020, compound

Product 1

HCID 178424019HCID 178424019, compoundYield 68.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

5-(4-Methylphenyl)-2-(4-nitrophenyl)-N-(2-thiazolyl)-imidazole-4-carboxamide (0.44 g) obtained in Example 19 was suspended in methanol and ice-cooled. To the suspension was added a solution of tin(II) chloride 6 hydrate (1.0 g) in 6 M hydrochloric acid solution (10 ml) and the mixture was refluxed under heating for 2.5 hr. Water was added and the mixture was neutralized with potassium carbonate and extracted with ethyl acetate. The organic layer was washed with water and, after drying, the solvent was evaporated under reduced pressure. The obtained residue was dissolved in ethyl acetate and 1 M hydrochloric acid—ether solution (5 ml) was added. The precipitated crystals were collected by filtration, and the obtained crude crystals were recrystallized from methanol to give 2-(4-aminophenyl)-5-(4-methylphenyl)-N-(2-thiazolyl)imidazole-4-carboxamide (0.28 g), melting point 244° C. (decomposition).

Workup

  1. temperatureice-cooled
  2. temperaturethe mixture was refluxed
  3. temperatureunder heating for 2.5 hr
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. customafter drying
  7. customthe solvent was evaporated under reduced pressure
  8. dissolutionThe obtained residue was dissolved in ethyl acetate
  9. addition1 M hydrochloric acid—ether solution (5 ml) was added
  10. filtrationThe precipitated crystals were collected by filtration
  11. customthe obtained crude crystals
  12. customwere recrystallized from methanol

Sources & evidence

ORD record
ord-8507978538a541229baa974ba54c099d
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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