1,4-Bis(bromomethyl)benzene → HCID 20322504, compound

HRID 840007Notes

Reaction equation

HRID 840007 reaction equation
[K].[CH2:2]([C:4]1([CH3:20])[NH:15][C:14]([CH2:17][CH3:18])([CH3:16])[CH2:13][C:6]2([NH:10][C:9](=[O:11])[NH:8][C:7]2=[O:12])[CH:5]1[CH3:19])[CH3:3].Br[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29]Br)=[CH:25][CH:24]=1>CN(C)C=O>[CH2:2]([C:4]1([CH3:20])[NH:15][C:14]([CH2:17][CH3:18])([CH3:16])[CH2:13][C:6]2([NH:10][C:9](=[O:11])[N:8]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][N:8]4[C:7](=[O:12])[C:6]5([CH2:13][C:14]([CH3:16])([CH2:17][CH3:18])[NH:15][C:4]([CH3:20])([CH2:2][CH3:3])[CH:5]5[CH3:19])[NH:10][C:9]4=[O:11])=[CH:25][CH:24]=3)[C:7]2=[O:12])[CH:5]1[CH3:19])[CH3:3]

Participants

5

Reactant 3

HCID 693351,4-Bis(bromomethyl)benzeneHCID 5462222PotassiumHCID 203401897,9-Diethyl-6,7,9-trimethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione

Product 1

HCID 20322504HCID 20322504, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To 80 ml of dimethylformamide were added 8.0 g of the potassium salt of 7,9-diethyl-6,7,9-trimethyl-1,3,8-triazaspiro[4.5]decane-2,4-dione and 3.1 g of α,α'-dibromo-p-xylene; the mixture was heated, with stirring, at 60° C for 3 hours. The mixture was then concentrated by evaporation under reduced pressure and the residue was dissolved in chloroform. The chloroform solution was washed with water and dried over magnesium sulphate; the chloroform was then removed. The residue was purified first by column chromatography on silica gel (eluent: a 6 : 3 : 0.5 by volume mixture of ethyl acetate, benzene and triethylamine) and then by recrystallization from ethanol, giving 5.0 g of Compound 43 as crystals melting at 272° - 274° C.

Workup

  1. temperaturethe mixture was heated
  2. concentrationThe mixture was then concentrated by evaporation under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform
  4. washThe chloroform solution was washed with water
  5. dry with materialdried over magnesium sulphate
  6. customthe chloroform was then removed
  7. customThe residue was purified first by column chromatography on silica gel (eluent
  8. additiona 6 : 3 : 0.5 by volume mixture of ethyl acetate, benzene and triethylamine) and then
  9. customby recrystallization from ethanol

Sources & evidence

ORD record
ord-fda41a52a5664b799f8d905c778db651
Source dataset
uspto-grants-1978_06
Patent number
US04097587

Reaction notes

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