Benzyl Chloride → HCID 13711993, compound

HRID 2372064Notes

Reaction equation

HRID 2372064 reaction equation
[H-].[Na+].[CH2:3]([N:5]1[C:9](=[O:10])[CH2:8][C:7]2([CH2:14][C:13](=[O:15])[NH:12][CH2:11]2)[C:6]1=[O:16])[CH3:4].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O>[CH2:3]([N:5]1[C:9](=[O:10])[CH2:8][C:7]2([CH2:14][C:13](=[O:15])[N:12]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:11]2)[C:6]1=[O:16])[CH3:4]

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 13711992HCID 13711992, compound

Product 1

HCID 13711993HCID 13711993, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A suspension of sodium hydride (2.20 g of 60% oil suspension (0.055 mole) washed with toluene) in 50 ml N,N-dimethylformamide was treated gradually with a solution of 10.0 g (0.051 mole) 2-ethyl-2,7-diazaspiro[4.4]nonane-1,3,8-trione in 100 ml N,N-dimethylformamide. After stirring 15 minutes, there was added dropwise 6.4 ml (0.055 mole) benzyl chloride and the mixture was stirred overnight, concentrated in vacuo and shaken with water-methylene chloride. The organic layers were dried, evaporated, and the product crystallized from toluene-hexane to afford 11.1 g of the title compound, mp 125-126.5° C.

Workup

  1. stirringthe mixture was stirred overnight
  2. concentrationconcentrated in vacuo
  3. stirringshaken with water-methylene chloride
  4. customThe organic layers were dried
  5. customevaporated
  6. customthe product crystallized from toluene-hexane

Sources & evidence

ORD record
ord-84f8334c95b44432b8e63859ad9a99a0
Source dataset
uspto-grants-1992_03
Patent number
US05097032

Reaction notes

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