Water → HCID 59728120, compound

HRID 2043332Notes

Reaction equation

HRID 2043332 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1.[CH:13]([C:15]1[N:16]=[CH:17][NH:18][CH:19]=1)=O.[BH4-].[Na+].O>CO>[N:18]1[CH:19]=[C:15]([CH2:13][NH:8][C:7]2[CH:9]=[CH:10][C:4]([O:3][C:2]([F:11])([F:12])[F:1])=[CH:5][CH:6]=2)[NH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 764281H-Imidazole-4-carbaldehydeHCID 6008484-(Trifluoromethoxy)anilineHCID 4311764Sodium borohydride

Product 1

HCID 59728120HCID 59728120, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-trifluoromethoxyaniline (0.89 g, 5 mmol) in methanol (5 ml) was added 4-formylimidazole (0.48 g, 5 mmol). After stirring the mixture overnight at 60° C. the solution was cooled and sodium borohydride (0.28 g, 7.5 mmol) were 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 (1.0 g, 78%); MS (ISP): 258.1 ((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-70765b53718a4d43962b7dcac248cab7
Source dataset
uspto-grants-2013_11
Patent number
US08586617B2

Reaction notes

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