Sodium Sulfate → HCID 23509648, compound

HRID 1882773Notes

Reaction equation

HRID 1882773 reaction equation
[C: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])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[C:16]1([C:12]2[CH:13]=[CH:14][CH:15]=[C:8]([NH:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:9]=2[CH2:10][NH2:11])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 24436Sodium Sulfate2×HCID 21226445Aluminium lithium hydrideHCID 23509657HCID 23509657, compound

Product 1

HCID 23509648HCID 23509648, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of example 1b above, 2-phenylamino-6-phenylbenzonitrile, (0.13 g, 0.48 mmol) was dissolved in dry tetrahydrofuran (20 mL) and stirred under argon in a room temperature water bath. Lithium aluminum hydride (0.182 g, 4.8 mmol) was added rapidly. After 5 minutes at room temperature the reaction mixture was heated to 60° C. for 2 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 gave the title compound as a white amorphous solid. mp 115-116° C.

Workup

  1. temperatureAfter 5 minutes at room temperature the reaction mixture was heated to 60° C. for 2 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customThe solvent was evaporated
  4. customthe residue triturated with ethyl acetate
  5. filtrationfiltered
  6. customevaporated
  7. washFlash chromatography on silica gel eluted with 0-2% methanol in methylene chloride

Sources & evidence

ORD record
ord-d73d66756be94823b76d19c61ba7a9ec
Source dataset
uspto-grants-2004_07
Patent number
US06759410B1

Reaction notes

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