Sodium hydride → 5-(2-Hydroxy-4-phenyl-2-trifluoromethyl-pentylamino)-phthalide

HRID 1066952Notes

Reaction equation

HRID 1066952 reaction equation
C([NH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:10](=[O:11])[O:9][CH2:8]2)(=O)C.[H-].[Na+].[OH:17][C:18]([C:40]([F:43])([F:42])[F:41])([CH2:31][CH:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH3:33])[CH2:19]OS(C1C=CC(C)=CC=1)(=O)=O>CN(C)C=O>[OH:17][C:18]([C:40]([F:41])([F:42])[F:43])([CH2:31][CH:32]([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[CH3:33])[CH2:19][NH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:10](=[O:11])[O:9][CH2:8]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5909685-Acetamido-phthalideHCID 185511734-Toluenesulfonic acid-(2-hydroxy-4-phenyl-2-trifluoromethyl-pentyl)-ester

Product 1

HCID 98427925-(2-Hydroxy-4-phenyl-2-trifluoromethyl-pentylamino)-phthalideYield 35.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

760 mg of 5-acetamido-phthalide in 20 ml of dimethylformamide is mixed at 0° C. with 144 mg of sodium hydride (80% in mineral oil), and, after 20 minutes, with 800 mg of 4-toluenesulfonic acid-(2-hydroxy-4-phenyl-2-trifluoromethyl-pentyl)-ester. After 16 hours at 60° C., the solvent is concentrated by evaporation in a vacuum, the residue is dissolved in ethyl acetate, washed with water, dried (Na2SO4) and concentrated by evaporation. After chromatography on silica gel with cyclohexane/ethyl acetate (2:1), 266 mg of 5-(2-hydroxy-4-phenyl-2-trifluoromethyl-pentylamino)-phthalide, melting point 110° C., is obtained.

Workup

  1. waitAfter 16 hours at 60° C.
  2. concentrationthe solvent is concentrated by evaporation in a vacuum
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-692a560ef18f4a229de8f0ea11f684a1
Source dataset
uspto-grants-2001_06
Patent number
US06245804B1

Reaction notes

Loading…