1-Bromo-3-chloropropane → HCID 22065888, compound

HRID 649755Notes

Reaction equation

HRID 649755 reaction equation
[CH3:1][N:2]1[C:6]2[C:7](=[O:14])[CH2:8][CH2:9][NH:10][S:11](=[O:13])(=[O:12])[C:5]=2[CH:4]=[CH:3]1.Br[CH2:16][CH2:17][CH2:18][Cl:19].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:19][CH2:18][CH2:17][CH2:16][N:10]1[CH2:9][CH2:8][C:7](=[O:14])[C:6]2[N:2]([CH3:1])[CH:3]=[CH:4][C:5]=2[S:11]1(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 12094993HCID 12094993, compound

Product 1

HCID 22065888HCID 22065888, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 214 mg (1 mmol) of Compound 14, 630 mg (4 mmol) of 1-bromo-3-chloropropane and 276 mg (2 mmol) of potassium carbonate in 5 ml of acetone was refluxed for 6 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/hexane=1/2), whereby 275 mg of the title compound were obtained (yield: 95%).

Workup

  1. temperaturewas refluxed for 6 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/hexane=1/2)

Sources & evidence

ORD record
ord-eea731ff06274fb38727889cfd857108
Source dataset
uspto-grants-2001_08
Patent number
US06271223B1

Reaction notes

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