1,2-Dibromoethane → HCID 86758885, compound

HRID 1862203Notes

Reaction equation

HRID 1862203 reaction equation
[OH-].[K+].Cl.[NH2:4]O.[CH3:6][O:7][N:8]=[C:9]([CH:29]=[C:30]([CH3:32])[CH3:31])[C:10](=[N:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH:21]=[N:22][O:23][CH2:24][C:25]([O:27][CH3:28])=O)[CH3:11].[C:33](=[O:36])([O-])[O-].[K+].[K+].BrCCBr>CO>[CH3:6][O:7][N:8]=[C:9]([CH:29]=[C:30]([CH3:32])[CH3:31])[C:10](=[N:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH:21]=[N:22][O:23][CH2:24][C:25]1[O:27][CH2:28][CH2:33][O:36][N:4]=1)[CH3:11]

Participants

7

Reactant 5

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 86758886HCID 86758886, compound

Product 1

HCID 86758885HCID 86758885, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 3.3 g (59 mmol) of potassium hydroxide in 20 ml of methanol was added to a solution of 1.75 g (25 mmol) of hydroxylamine hydrochloride in 20 ml of methanol. The mixture was stirred at room temperature for 5 minutes, 4.5 g (12 mmol) of 5-methylhex-4-ene-2,3-dione 2-(O-(2-(methoxycarbonylmethoxyiminomethyl)benzyl)oxime) 3-(O-methyloxime) were then added and the mixture was stirred at 40° C. for 1 h. 1.8 g (13 mmol) of potassium carbonate and 5.1 ml (59 mmol) of 1,2-dibromoethane were subsequently added. The reaction mixture was stirred at room temperature for 18 h and then concentrated under reduced pressure, and the residue was purified by chromatography. This gave 0.6 g of the title compound as an oil.

Workup

  1. stirringthe mixture was stirred at 40° C. for 1 h
  2. stirringThe reaction mixture was stirred at room temperature for 18 h
  3. concentrationconcentrated under reduced pressure
  4. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-dc405283edd74e2e94a8b276bf9b703f
Source dataset
uspto-grants-2003_03
Patent number
US06537989B1

Reaction notes

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