Stannous chloride dihydrate → HCID 69563721, compound

HRID 729994Notes

Reaction equation

HRID 729994 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[NH:13][C:12]([C:14]2[N:19]=[C:18]([NH:20][S:21]([CH:24]([CH3:26])[CH3:25])(=[O:23])=[O:22])[C:17]([N+:27]([O-])=O)=[CH:16][CH:15]=2)=[C:11]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:10]=1.O.O.[Sn](Cl)Cl>CCO>[NH2:27][C:17]1[C:18]([NH:20][S:21]([CH:24]([CH3:26])[CH3:25])(=[O:23])=[O:22])=[N:19][C:14]([C:12]2[NH:13][C:9]([C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=3[Cl:8])=[N:10][C:11]=2[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 86626985HCID 86626985, compound

Product 1

HCID 69563721HCID 69563721, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Heat a mixture of propane-2-sulfonic acid {6-[2-(2,6-dichlorophenyl)-5-phenyl-3H-imidazol-4-yl]-3-nitropyridin-2-yl}amide (0.262 g, 0.49 mmol) and tin (II) chloride dihydrate (0.55 g, 2.46 mmol) in EtOH (10 mL) at 100° C. for 1 h. Cool to RT and concentrate to a slurry. Pour the reaction mixture into saturated NaHCO3 (20 mL) and add a filtering agent. Filter and wash with EtOAc. Separate the layers and extract successively with saturated NaHCO3 and saturated aqueous NaCl. Dry the organic layer over Na2SO4 and concentrate to give the title compound (0.21 g, 85%).

Workup

  1. temperatureHeat
  2. concentrationconcentrate to a slurry
  3. additionPour the reaction mixture into saturated NaHCO3 (20 mL)
  4. additionadd a filtering agent
  5. filtrationFilter
  6. washwash with EtOAc
  7. customSeparate the layers
  8. extractionextract successively with saturated NaHCO3 and saturated aqueous NaCl
  9. dry with materialDry the organic layer over Na2SO4
  10. concentrationconcentrate

Sources & evidence

ORD record
ord-10f2fea5de6947adb3e9f5c036feb297
Source dataset
uspto-grants-2009_09
Patent number
US07582652B2

Reaction notes

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