Sodium Sulfate → HCID 15027427, compound

HRID 1646705Notes

Reaction equation

HRID 1646705 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[NH:17][C:18](=O)[CH:19]([CH3:21])[CH3:20].S([O-])([O-])(=O)=O.[Na+].[Na+]>CCOCC.ClCCl>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][OH:8])=[C:11]([NH:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH:12]=1

Participants

6

Reactant 3

HCID 24436Sodium SulfateHCID 19801336HCID 19801336, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15027427HCID 15027427, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3.96 g (105 mmol) of lithium aluminum hydride in 200 ml of dry ether was dropwise added under chilling with ice for 15 min. a solution of 9.50 g (37 mmol) of methyl-4-chloro-2-(isobutyrylamino)benzoate obtained in b) above in a mixture of 20 ml of dry dichloromethane and 20 ml of dry ether. The mixture was then stirred for 30 min., and heated under reflux for 30 min. To the mixture was dropwise added under chilling with ice a saturated aqueous sodium sulfate. The organic portion was taken out by decantation, and dried over anhydrous sodium sulfate. The solvent was distilled off to leave 7.28 g of the desired compound as a residual colorless oil.

Workup

  1. additionwas dropwise added
  2. customobtained in b)
  3. temperatureheated
  4. temperatureunder reflux for 30 min
  5. additionTo the mixture was dropwise added
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-1995196e1a40412e9ba637626aa1523f
Source dataset
uspto-grants-1993_01
Patent number
US05180836

Reaction notes

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