Sodium hydride → 3-{4-[15-(Trifluoromethyl)pentadecylamino]benzoyl}-2,4-pentanedione

HRID 1659937Notes

Reaction equation

HRID 1659937 reaction equation
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH3:5].[H-].[Na+].Cl.[F:11][C:12]([F:39])([F:38])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][NH:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1>COCCOC>[F:11][C:12]([F:39])([F:38])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][NH:28][C:29]1[CH:37]=[CH:36][C:32]([C:33]([CH:3]([C:2](=[O:7])[CH3:1])[C:4](=[O:6])[CH3:5])=[O:34])=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31261AcetylacetoneHCID 205493174-[15-(Trifluoromethyl)pentadecylamino]benzoyl chloride hydrochloride

Product 1

HCID 205493713-{4-[15-(Trifluoromethyl)pentadecylamino]benzoyl}-2,4-pentanedione

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

A solution of 28.4 g. of 2,4-pentanedione and 20 ml. of 1,2-dimethoxyethane is added to a suspension of 13.6 g. of sodium hydride in 220 ml. of 1,2-dimethoxyethane under argon. A solution of 28.7 g. of 4-[15-(trifluoromethyl)pentadecylamino]benzoyl chloride hydrochloride in 1,2-dimethoxyethane is then added. The reaction mixture is stirred at room temperature for 12 hours, cooled, poured on ice-and extracted with ether. The ether solution is washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated. The residue is then chromatographed over silica gel to yield the product as a white solid.

Workup

  1. temperaturecooled
  2. additionpoured on ice-
  3. extractionextracted with ether
  4. washThe ether solution is washed with water and saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue is then chromatographed over silica gel

Sources & evidence

ORD record
ord-61eebcda0e484f0b85cc614511738b00
Source dataset
uspto-grants-1981_12
Patent number
US04305959

Reaction notes

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