Tin dichloride dihydrate → HCID 178507426, compound

HRID 427393Notes

Reaction equation

HRID 427393 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[NH:6][C:7]([C:9]3[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=3)=[N:8][C:4]=2[CH:3]=1.Cl[Sn]Cl.O>CC(O)=O.Cl>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[NH:6][C:7]([C:9]3[CH:10]=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=3)=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 43835034Tin dichloride dihydrateHCID 178526536HCID 178526536, compound

Product 1

HCID 178507426HCID 178507426, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

In 500 mL round bottom flask was suspended 5-Chloro-2-(4-nitro-phenyl)-1H-benzoimidazole (4.23 g, 13.66 mmol) in AcOH (30 mL) at 0° C., and to the suspension was added dropwise SnCl2.H2O (9.4 g, 41.66 mmol), in HCl (15 mL). After the addition, the ice bath was removed and the mixture was allowed to stir at room temperature overnight (16 h). The mixture was poured onto ice, and NaOH (50% aq.) was slowly added to pH 12. Then the mixture was extracted with EtOAc (4×150 mL). The combined organic layers were washed with brine, dried over NaSO4 and filtered, the solvent was evaporated to yield the product as an orange oil. The oil was dissolved in EtOAc and washed with HCl (1.0 N, 100 mL) and the product was isolated as HCl salt (2.13 g, 67%).

Workup

  1. customIn 500 mL round bottom flask was suspended
  2. additionAfter the addition
  3. customthe ice bath was removed
  4. additionThe mixture was poured onto ice, and NaOH (50% aq.)
  5. additionwas slowly added to pH 12
  6. extractionThen the mixture was extracted with EtOAc (4×150 mL)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over NaSO4
  9. filtrationfiltered
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-53070be51b5e46829ef0ba958104869d
Source dataset
uspto-grants-2001_11
Patent number
US06313117B1

Reaction notes

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