Hydrochloric Acid → HCID 71294558, compound

HRID 508580Notes

Reaction equation

HRID 508580 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1)#[N:2].C(Br)(Br)Br.[OH-].[K+].Cl.C([OH:20])C.[O:21]1[CH2:26][CH2:25][O:24][CH2:23]C1>O.C(O)C>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][CH2:23][O:24][CH2:25][C:26]([OH:21])=[O:20])=[CH:5][CH:4]=1)#[N:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 5558BromoformHCID 14797Potassium HydroxideHCID 660424-CyanobenzaldehydeHCID 22560076Dioxan ethanol

Product 1

HCID 71294558HCID 71294558, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4-Cyanobenzaldehyde (3.0 g) was dissolved in a 1:1 mixed solution of ethanol/1,4-dioxane (80 mL), and bromoform (7.0 g) was added thereto under ice cooling. Subsequently, an ethanol solution (40 mL) of potassium hydroxide (7.6 g) was carefully added thereto, and the mixture was stirred for 6 hours at room temperature. After distilling off the solvent under reduced pressure, the residue thus obtained was diluted with water. The mixture was acidified with a 2 mol/L hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (50% to 100% ethyl acetate/hexane), and the title compound (2.6 g) was obtained as a crude product.

Workup

  1. additionwas added
  2. distillationAfter distilling off the solvent under reduced pressure
  3. customthe residue thus obtained
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationAfter distilling off the solvent under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (50% to 100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7378be704235403b91ef000e1dce154c
Source dataset
uspto-grants-2015_08
Patent number
US09096531B2

Reaction notes

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