Sodium Sulfate → HCID 22341437, compound

HRID 585001Notes

Reaction equation

HRID 585001 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[C:17]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:18]=[C:19]([C:21]([NH:23][CH3:24])=O)[CH:20]=2)=[CH:11][CH:10]=1)=[O:8].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:24][NH:23][CH2:21][C:19]1[CH:20]=[C:15]([C:12]2[CH:11]=[CH:10][C:9]([CH2:7][OH:8])=[CH:14][CH:13]=2)[CH:16]=[C:17]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:18]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 22341484HCID 22341484, compound

Product 1

HCID 22341437HCID 22341437, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

1 g (26 mmol) of lithium aluminum hydride in 20 ml of tetrahydrofuran are introduced into a round-bottomed flask under a stream of nitrogen. The medium is cooled to 0° C. and a solution of 1.4 g (4.4 mmol) of 4″-formyl-N-methyl[1,1′;3′,1″]terphenyl-5′-carboxamide in 30 ml of tetrahydrofuran is added dropwise. The reaction medium is refluxed for 48 hours. It is then allowed to cool to room temperature and aqueous sodium sulfate solution is added dropwise. After 30 minutes, the medium is acidified to pH 5 and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and then evaporated. The residue is purified by chromatography on a column of silica eluted with a dichloromethane/ethanol mixture (9/1) and 660 mg (49%) of the expected product are obtained in the form of a white solid.

Workup

  1. temperatureThe reaction medium is refluxed for 48 hours
  2. temperatureto cool to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by chromatography on a column of silica
  8. washeluted with a dichloromethane/ethanol mixture (9/1) and 660 mg (49%) of the expected product
  9. customare obtained in the form of a white solid

Sources & evidence

ORD record
ord-bac5060a14a741899ffcf9802d1f73d2
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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