Water → HCID 12387514, compound

HRID 2367862Notes

Reaction equation

HRID 2367862 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]([CH3:19])([C:12](=[O:18])[CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:11].C([O-])(=O)C.[NH4+].O>CC(C)(C)C#N>[Br:1][CH:13]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12](=[O:18])[C:10]([CH3:19])([CH3:9])[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 67184N-bromobutanimide2×HCID 1366702,2,5,5-Tetramethyl-3-hexanoneHCID 517165Ammonium Acetate2×

Product 1

HCID 12387514HCID 12387514, compound

Reagents, catalysts & solvents 1

HCID 12416PivalonitrileSolvent

Procedure

24 g of N-bromosuccinimide (0.1344 mol) was added to 10 g of 2,2,5,5-Tetramethyl-3-hexanone (0.064 mol) in 50 mL of trimethylacetonitrile. To this mixture, 10 g of ammonium acetate (0.1344 mol) was added within 5 minutes. This mixture was refluxed overnight then filtered. To the filtrate, 24 g of N-bromosuccinimide (0.1344 mol) and 10 g of ammonium acetate (0.1344 mol) was added, then refluxed for 5 hours. The reaction mixture was then cooled, 600 mL of water added, and the resulting mixture then filtered. The aqueous layer was washed three times with 50 ml of hexanes. The hexane fractions were then combined, washed three times with 50 ml of with water, then dried with anhydrous magnesium sulfate. Product was collected by distilling off the hexane at atmospheric pressure.

Workup

  1. temperatureThis mixture was refluxed overnight
  2. filtrationthen filtered
  3. temperaturerefluxed for 5 hours
  4. temperatureThe reaction mixture was then cooled
  5. filtrationthe resulting mixture then filtered
  6. washThe aqueous layer was washed three times with 50 ml of hexanes
  7. washwashed three times with 50 ml of with water
  8. dry with materialdried with anhydrous magnesium sulfate
  9. customProduct was collected
  10. distillationby distilling off the hexane at atmospheric pressure

Sources & evidence

ORD record
ord-4e5e363dbe2647739e1238344514c04d
Source dataset
uspto-grants-2014_04
Patent number
US08703103B2

Reaction notes

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