1,3-Dibromopropane → HCID 15550033, compound

HRID 1168596Notes

Reaction equation

HRID 1168596 reaction equation
[CH3:1][N:2]1[C:6]2[C:7](=[O:13])[CH2:8][NH:9][S:10](=[O:12])(=[O:11])[C:5]=2[CH:4]=[CH:3]1.[Br:14][CH2:15][CH2:16][CH2:17]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:14][CH2:15][CH2:16][CH2:17][N:9]1[CH2:8][C:7](=[O:13])[C:6]2[N:2]([CH3:1])[CH:3]=[CH:4][C:5]=2[S:10]1(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 15550036HCID 15550036, compound

Product 1

HCID 15550033HCID 15550033, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 500 mg (2.5 mmol) of Compound 13, 2.5 g (12.5 mmol) of 1,3-dibromopropane and 690 mg (5 mmol) of potassium carbonate in 25 ml of acetone was refluxed for 12 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column (eluent: ethyl acetate/methylene chloride =1/40), whereby 274 mg of the title compound were obtained (yield: 34%).

Workup

  1. temperaturewas refluxed for 12 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by chromatography on a silica gel column (eluent: ethyl acetate/methylene chloride =1/40)

Sources & evidence

ORD record
ord-77d8eae16046403ba6aaba2072357233
Source dataset
uspto-grants-2003_09
Patent number
US06624314B2

Reaction notes

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