Sodium hydride → HCID 20331148, compound

HRID 2057677Notes

Reaction equation

HRID 2057677 reaction equation
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH3:5].[H-].[Na+].Cl.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]#[C:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][NH:31][C:32]2[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=2)=[CH:14][CH:13]=1>COCCOC>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]#[C:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][NH:31][C:32]2[CH:40]=[CH:39][C:35]([C:36]([CH:3]([C:2](=[O:7])[CH3:1])[C:4](=[O:6])[CH3:5])=[O:37])=[CH:34][CH:33]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31261AcetylacetoneHCID 20331330HCID 20331330, compound

Product 1

HCID 20331148HCID 20331148, compound

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-[13-(4-chlorophenyl)tridec-12-ynylamino]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 3-{4'-[13-(4-chlorophenyl)tridec-12-ynylamino]benzoyl} 2,4-pentanedione.

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-7d95ecc82aa14211bad4e7958ea704ce
Source dataset
uspto-grants-1980_07
Patent number
US04211783

Reaction notes

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