Sodium Sulfate → HCID 23509646, compound

HRID 1882764Notes

Reaction equation

HRID 1882764 reaction equation
[CH:1]1([NH:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:9]=2[C:10]#[N:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH:1]1([NH:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:9]=2[CH2:10][NH2:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 24436Sodium Sulfate2×HCID 21226445Aluminium lithium hydrideHCID 23509651HCID 23509651, compound

Product 1

HCID 23509646HCID 23509646, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of example 1b above, 2-cyclohexylamino-6-phenylbenzonitrile, (0.095 g, 0.34 mmol) was dissolved in dry tetrahydrofuran (20 mL) and stirred under argon at room temperature. Lithium aluminum hydride (0.136 g, 3.4 mmol) was added and the mixture heated to reflux under argon for 9 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 0-2% methanol in methylene chloride followed by recrystallization from ethyl acetate/hexane gave the title compound as a white crystalline solid. mp 95-96° C.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux under argon for 9 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 0-2% methanol in methylene chloride
  9. customfollowed by recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-f9a4b199236d449fad2e37c422e4f8ff
Source dataset
uspto-grants-2004_07
Patent number
US06759410B1

Reaction notes

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