Sodium Sulfate → HCID 23509655, compound

HRID 1882770Notes

Reaction equation

HRID 1882770 reaction equation
[CH2:1]([NH:8][C:9]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]=1[C:11]#[N:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH2:1]([NH:8][C:9]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:10]=1[CH2:11][NH2:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24436Sodium Sulfate2×HCID 21226445Aluminium lithium hydrideHCID 23509649HCID 23509649, compound

Product 1

HCID 23509655HCID 23509655, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of example 7a above, 2-benzylamino-6-phenylbenzonitrile, was dissolved in dry tetrahydrofuran (10 mL) and stirred under argon at room temperature. Lithium aluminum hydride (0.175 g, 4.3 mmol) was added and the mixture heated to reflux under argon for 20 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 to give the title compound. ES (+) MS m/e=272(M-NH2+)

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux under argon for 20 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

Sources & evidence

ORD record
ord-6640387a5193496e9fb4133c0a180060
Source dataset
uspto-grants-2004_07
Patent number
US06759410B1

Reaction notes

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