Stannous chloride dihydrate → HCID 68665521, compound

HRID 1893477Notes

Reaction equation

HRID 1893477 reaction equation
[Br:1][C:2]1[C:3]([C:16]([F:19])([F:18])[F:17])=[CH:4][C:5]([N+:13]([O-])=O)=[C:6]([N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)[CH:7]=1.O.O.Cl[Sn]Cl>C(O)C>[Br:1][C:2]1[C:3]([C:16]([F:19])([F:18])[F:17])=[CH:4][C:5]([NH2:13])=[C:6]([N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)[CH:7]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 59333299HCID 59333299, compound

Product 1

HCID 68665521HCID 68665521, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-[5-bromo-2-nitro-4-(trifluoromethyl)phenyl]-1H-imidazole (15.50 g, 0.0461 mol) is stirred with SnCl2.2H2O (51.77 g, 0.2274 mol) in ethanol (78 mL) at 80° C. for 2 hours. After cooling down to room temperature, the mixture is concentrated and partitioned between water (200 mL) and ethyl acetate (250 mL). Sodium hydrogencarbonate powder is added to adjust the pH to 8. The milky suspension is filtrated, the cake is washed with ethyl acetate and the combined organic phases are washed with water and dried over sodium sulfate. Concentration affords the title compound as a pale yellow solid (12.70 g, 90.0%)

Workup

  1. concentrationthe mixture is concentrated
  2. custompartitioned between water (200 mL) and ethyl acetate (250 mL)
  3. additionSodium hydrogencarbonate powder is added
  4. filtrationThe milky suspension is filtrated
  5. washthe cake is washed with ethyl acetate
  6. washthe combined organic phases are washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationConcentration

Sources & evidence

ORD record
ord-00980ea6bfd44818a11b066a9c47bd8a
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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