Water → HCID 62761381, compound

HRID 2043334Notes

Reaction equation

HRID 2043334 reaction equation
[Cl:1][C:2]1[C:3]([F:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[CH:10]([C:12]1[N:13]=[CH:14][NH:15][CH:16]=1)=O.[BH4-].[Na+].O>CO>[Cl:1][C:2]1[C:3]([F:9])=[C:4]([NH:5][CH2:10][C:12]2[NH:13][CH:14]=[N:15][CH:16]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 750143-Chloro-2-fluoroanilineHCID 764281H-Imidazole-4-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 62761381HCID 62761381, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-chloro-2-fluoroaniline (0.44 g, 3 mmol) in methanol (5 ml) was added 4-formylimidazole (0.29 g, 3 mmol). After stirring the mixture overnight at 60° C. the solution was cooled and sodium borohydride (0.57 g, 15 mmol) was added. The reaction mixture was stirred at room temperature for 4 hours. Then water was added and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with water, dried over magnesium sulfate and evaporated. The residue was purified by column filtration (heptane/ethyl acetate=1:1) to yield a light yellow liquid (0.55 mg, 81%); MS (ISP): 226.3 ((M+H)+.).

Workup

  1. temperaturewas cooled
  2. stirringThe reaction mixture was stirred at room temperature for 4 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. filtrationThe residue was purified by column filtration (heptane/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-4ec243d0d1824efabf70784fbff1ef4d
Source dataset
uspto-grants-2013_11
Patent number
US08586617B2

Reaction notes

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