3-Methyl-2-butanone → HCID 15521427, compound

HRID 1383383Notes

Reaction equation

HRID 1383383 reaction equation
[CH:1]([C:4]([CH3:6])=O)([CH3:3])[CH3:2].Br.CC(O)=O.BrBr.[C:14]([CH2:17][O:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH:22]=[O:23])(=[S:16])[NH2:15].C(=O)([O-])O.[Na+]>CO.O>[CH:1]([C:4]1[N:15]=[C:14]([CH2:17][O:18][C:19]2[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=2)[CH:22]=[O:23])[S:16][CH:6]=1)([CH3:3])[CH3:2]

Participants

8

Reactant 5

HCID 112513-Methyl-2-butanoneHCID 24408BromineHCID 516892Sodium BicarbonateHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 22617025HCID 22617025, compound

Product 1

HCID 15521427HCID 15521427, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Then, 32.9 g (0.38 mol) of methyl isopropyl ketone was dissolved in 291 ml of methanol and mixed with 2.9 ml of 25% HBr-AcOH under cooling with ice. 18.7 ml (0.36 mol) of bromine was added dropwise under cooling with ice, and the reaction solution was stirred for 2 hours. The reaction solution was stirred together with water at room temperature for 30 minutes and then together with 3-(thiocarbamoylmethoxy)benzaldehyde at room temperature for 5.5 hours. Water and saturated sodium hydrogen carbonate were added to adjust the pH to 8.0, and the reaction solution was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo for removal of the solvent, and the residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=20:1) to give 64.3 g of the title compound in a yield of 68%.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. extractionthe reaction solution was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo for removal of the solvent
  7. customthe residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-0206e8c231664f06b39f21ec4e0692a8
Source dataset
uspto-grants-2001_07
Patent number
US06255321B1

Reaction notes

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