Stannous Chloride → HCID 178507459, compound

HRID 1595398Notes

Reaction equation

HRID 1595398 reaction equation
[C:1]1([C:11]2[NH:12][C:13]([C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[CH:26][CH:25]=3)=[C:14]([C:16]([NH:18][C:19]3[S:20][CH:21]=[CH:22][N:23]=3)=[O:17])[N:15]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Sn](Cl)Cl>CO.Cl>[NH2:30][C:27]1[CH:26]=[CH:25][C:24]([C:13]2[NH:12][C:11]([C:1]3[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:4]=[CH:3][CH:2]=3)=[N:15][C:14]=2[C:16]([NH:18][C:19]2[S:20][CH:21]=[CH:22][N:23]=2)=[O:17])=[CH:29][CH:28]=1

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 178522567HCID 178522567, compound

Product 1

HCID 178507459HCID 178507459, compoundYield 24.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

2-(1-Naphthyl)-5-(4-nitrophenyl)-N-(2-thiazolyl)imidazole-4-carboxamide (1.22 g) obtained in Example 18 was suspended in methanol and ice-cooled. To the suspension was added a solution of tin(II) chloride 6 hydrate (3.0 g) in 6 M hydrochloric acid (30 ml) and the mixture was refluxed under heating for 1.5 hr. The precipitated white crystals were collected by filtration and the crystals were dissolved in ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium hydrogencarbonate solution and water, and dried. To the ethyl acetate layer was added 1 M hydrochloric acid—ether and the precipitated crystals were collected by filtration. The obtained crude crystals were recrystallized from methanol to give 5-(4-aminophenyl)-2-(1-naphthyl)-N-(2-thiazolyl)imidazole-4-carboxamide (0.28 g).

Workup

  1. temperatureice-cooled
  2. temperaturethe mixture was refluxed
  3. temperatureunder heating for 1.5 hr
  4. filtrationThe precipitated white crystals were collected by filtration
  5. dissolutionthe crystals were dissolved in ethyl acetate
  6. washThe ethyl acetate layer was washed with saturated aqueous sodium hydrogencarbonate solution and water
  7. customdried
  8. additionTo the ethyl acetate layer was added 1 M hydrochloric acid—ether
  9. filtrationthe precipitated crystals were collected by filtration
  10. customThe obtained crude crystals
  11. customwere recrystallized from methanol

Sources & evidence

ORD record
ord-8b9e540969bd4e5eb9124f576c40c7ee
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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