Sodium Sulfate → HCID 23509656, compound

HRID 1882766Notes

Reaction equation

HRID 1882766 reaction equation
[CH:1]([NH:4][C:5]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:6]=1[C:7]#[N:8])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH:1]([NH:4][C:5]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:6]=1[CH2:7][NH2:8])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24436Sodium Sulfate2×HCID 21226445Aluminium lithium hydrideHCID 23509647HCID 23509647, compound

Product 1

HCID 23509656HCID 23509656, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of example 2a above, 2-isopropylamino-6-phenylbenzonitrile, (0.095 g, 0.4 mmol) was dissolved in dry tetrahydrofuran (20 mL) and stirred under argon at room temperature. Lithium aluminum hydride (0.160 g, 4 mmol) was added and the mixture heated to reflux under argon for 16 hours. The reaction mixture was cooled to room temperature and anhydrous sodium sulfate was added followed by the addition of a freshly prepared saturated solution of anhydrous sodium sulfate. The solvent was evaporated and the residue triturated with ethyl acetate, filtered and evaporated. Flash chromatography on silica gel eluted with 0-3% methanol in methylene chloride followed by recrystallization from ethyl acetate/hexane gave the title compound as a white crystalline solid. ES (+) MS m/e=241 (MH+)

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux under argon for 16 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customThe solvent was evaporated
  5. customthe residue triturated with ethyl acetate
  6. filtrationfiltered
  7. customevaporated
  8. washFlash chromatography on silica gel eluted with 0-3% methanol in methylene chloride
  9. customfollowed by recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-39333135cd214cd3ae22bb428c468b84
Source dataset
uspto-grants-2004_07
Patent number
US06759410B1

Reaction notes

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