Sodium Sulfate → HCID 22136225, compound

HRID 1826837Notes

Reaction equation

HRID 1826837 reaction equation
[O:1]([C:8]1[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[C:9]=1[C:10]#[N:11])[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>[O:1]([C:8]1[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[C:9]=1[CH2:10][NH2:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 22136223HCID 22136223, compound

Product 1

HCID 22136225HCID 22136225, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product of example 2a above, 2-phenoxy-6-aminobenzonitrile, (1.5 g, 7.14 mmol) was dissolved in dry tetrahydrofuran (50 mL) and stirred under argon in a room temperature water bath. Lithium aluminum hydride (0.53 g, 14.0 mmol) was added in portions over 10 minutes. The reaction mixture was heated to 60° C. for 1 hour. The reaction mixture was cooled to room temperature and anhydrous sodium sulfate was added followed by quenching 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 gave the title compound as a white amorphous solid. Recrystallization from carbon tetrachloride, hexane gave a white crystalline solid. mp 69–71° C.

Workup

  1. temperatureThe reaction mixture was heated to 60° C. for 1 hour
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customby quenching by the addition of a freshly prepared saturated solution of anhydrous sodium sulfate
  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

Sources & evidence

ORD record
ord-d0fd465b07f44f4cb9303ee0931784fc
Source dataset
uspto-grants-2006_05
Patent number
US07053099B1

Reaction notes

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