Benzyl Bromide → HCID 70589902, compound

HRID 1732427Notes

Reaction equation

HRID 1732427 reaction equation
[CH3:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([N:10]([CH:24]2[CH2:29][C:28]([CH3:31])([CH3:30])[N:27]([CH3:32])[C:26]([CH3:34])([CH3:33])[CH2:25]2)[C:11](=[O:23])[CH:12]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:13]([OH:15])=[O:14])[CH2:4][C:3]1([CH3:36])[CH3:35].[H-].[Na+].[CH2:39](Br)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C1(C)C=CC=CC=1.CN(C)C=O>[CH3:32][N:27]1[C:26]([CH3:34])([CH3:33])[CH2:25][CH:24]([N:10]([CH:5]2[CH2:6][C:7]([CH3:8])([CH3:9])[N:2]([CH3:1])[C:3]([CH3:36])([CH3:35])[CH2:4]2)[C:11](=[O:23])[C:12]([CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)([CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:13]([OH:15])=[O:14])[CH2:29][C:28]1([CH3:31])[CH3:30]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydride2×HCID 70592349HCID 70592349, compound

Product 1

HCID 70589902HCID 70589902, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent3×HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

With stirring, a solution of 20 g of benzylmalonic bis-(1,2,2,6,6-pentamethyl-4-piperidinyl)-amide in 50 ml of toluene and 100 ml of dimethylformamide is added dropwise in the course of about 1/2 hour to a suspension of oil-free sodium hydride (0.97 g) in toluene (20 ml). After the addition of the amide, the reaction mixture is stirred for a further 20 hours at 60° C. until all the sodium hydride is reacted. A solution of 7.7 g of benzyl bromide in 10 ml of toluene is then added dropwise to the reaction mixture at room temperature in the course of 40 minutes, the temperature is raised to 70° C. and stirring is continued for 12 hours at this temperature. For working up, the reaction solution is filtered warm to remove precipitated sodium bromide, the residue is washed well with chloroform and the combined filtrates are freed as completely as possible from all solvents by rotary evaporation. The residue is dissolved in 400 ml of chloroform, the solution is extracted repeatedly with water, dried over sodium sulphate and the solvent removed in vacuo. The crystalline residue is recrystallised once in toluene and once in benzene, affording dibenzylmalonic bis-(1,2,2,6,6-pentamethyl-4-piperidinyl)-amide with a melting point of 275°-277° C. (Stabiliser 4).

Workup

  1. customis reacted
  2. stirringstirring
  3. filtrationthe reaction solution is filtered
  4. temperaturewarm
  5. customto remove
  6. customprecipitated sodium bromide
  7. washthe residue is washed well with chloroform
  8. customby rotary evaporation
  9. dissolutionThe residue is dissolved in 400 ml of chloroform
  10. extractionthe solution is extracted repeatedly with water
  11. dry with materialdried over sodium sulphate
  12. customthe solvent removed in vacuo
  13. customThe crystalline residue is recrystallised once in toluene and once in benzene

Sources & evidence

ORD record
ord-61bbfc99dba04088bda792468e60aac3
Source dataset
uspto-grants-1980_12
Patent number
US04237297

Reaction notes

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