Water → HCID 22449363, compound

HRID 490221Notes

Reaction equation

HRID 490221 reaction equation
[H-].[Na+].[C:3](#[N:7])[CH2:4][C:5]#[N:6].[C:8]1([CH2:14][C:15](Cl)=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>O1CCCC1>[OH:16][C:15](=[C:4]([C:3]#[N:7])[C:5]#[N:6])[CH2:14][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7679Phenylacetyl chlorideHCID 8010MalononitrileHCID 24758Sodium hydride

Product 1

HCID 22449363HCID 22449363, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

A suspension of sodium hydride (12.5 g) in tetrahydrofuran (188 mL) was cooled to 0° C. A solution of malononitrile (10.3 g) in tetrahydrofuran (65 mL) was added dropwise thereto over a period of 1 hour. After stirring the reaction mixture at room temperature for 1 hour, it was again cooled to 0° C., and then a solution of 2-phenylacetyl chloride (24.2 g) in tetrahydrofuran (52 mL) was added dropwise thereto over a period of 80 minutes. After stirring the reaction mixture at room temperature for 49 hours, water (26 mL) was added to the reaction solution. The solvent was distilled off under reduced pressure, diethyl ether (130 mL) and 1 mol/L hydrochloric acid (130 mL) were added to the residue and extraction was performed with diethyl ether. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain the title compound as a crude product (31.2 g).

Workup

  1. temperatureit was again cooled to 0° C.
  2. waitover a period of 80 minutes
  3. stirringAfter stirring the reaction mixture at room temperature for 49 hours
  4. distillationThe solvent was distilled off under reduced pressure, diethyl ether (130 mL) and 1 mol/L hydrochloric acid (130 mL)
  5. additionwere added to the residue and extraction
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-af29c5c54e85493abdbbce3345f6ac7a
Source dataset
uspto-grants-2009_05
Patent number
US07528140B2

Reaction notes

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