Ethylene Glycol → HCID 57980226, compound

HRID 1867780Notes

Reaction equation

HRID 1867780 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:7](Cl)=[O:8])([O-:3])=[O:2].C(N(CC)CC)C.[CH2:23]([OH:26])[CH2:24][OH:25].[Br:27][C:28]([CH3:33])([CH3:32])[C:29](Br)=[O:30]>C1COCC1>[Br:27][C:28]([CH3:33])([CH3:32])[C:29]([O:25][CH2:24][CH2:23][O:26][C:7](=[O:8])[C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=1)=[O:30]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 74323,5-Dinitrobenzoyl chlorideHCID 8471Triethylamine2×HCID 886852-Bromo-2-methylpropionyl bromide

Product 1

HCID 57980226HCID 57980226, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3,5-dinitrobenzoyl chloride (10 g, 0.043 mol) in 80 ml anhydrous THF was added triethylamine (4.83 g, 0.048 mol) followed by anhydrous ethylene glycol (24 ml, 0.43 mol). After 1 h, the solution was quenched with 200 ml water and extracted into ethyl acetate (3×150 ml). The organics were washed with 100 ml each 10% KOH, water, 1M HCl, brine, dried over magnesium sulfate and concentrated to 8.8 g. To this material, dissolved in 50 ml anhydrous THF and cooled in an ice bath, was added triethylamine (3.83 g, 0.038 mol) and then bromoisobutyryl bromide (8.70 g, 0.038 mol). After 0.5 h, the solution was quenched with 100 ml water and extracted into ethyl acetate (3×100 ml). The organics were washed with 100 ml each 10% KOH, water, 1M HCl, brine, dried over magnesium sulfate and concentrated. Purification by column chromatography yielded 9 gm of product, 96% pure by HPLC.

Workup

  1. customthe solution was quenched with 200 ml water
  2. extractionextracted into ethyl acetate (3×150 ml)
  3. washThe organics were washed with 100 ml each 10% KOH, water, 1M HCl, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to 8.8 g
  6. dissolutionTo this material, dissolved in 50 ml anhydrous THF
  7. temperaturecooled in an ice bath
  8. waitAfter 0.5 h
  9. customthe solution was quenched with 100 ml water
  10. extractionextracted into ethyl acetate (3×100 ml)
  11. washThe organics were washed with 100 ml each 10% KOH, water, 1M HCl, brine
  12. dry with materialdried over magnesium sulfate
  13. concentrationconcentrated
  14. customPurification by column chromatography

Sources & evidence

ORD record
ord-30bc9a274bea4e26add46736e803c865
Source dataset
uspto-grants-2009_12
Patent number
US07632875B2

Reaction notes

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