1-Bromo-3-chloropropane → HCID 22065897, compound

HRID 1828236Notes

Reaction equation

HRID 1828236 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[CH2:15][CH2:16][CH2:17][Cl:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:18][CH2:17][CH2:16][CH2:15][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 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 15550036HCID 15550036, compound

Product 1

HCID 22065897HCID 22065897, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 200 mg (1 mmol) of Compound 13, 189 mg (1.2 mmol) of 1-bromo-3-chloropropane and 345 mg (2.5 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/methylene chloride=1/30), whereby 125 mg of the title compound were obtained (yield: 45%).

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/methylene chloride=1/30)

Sources & evidence

ORD record
ord-b8bb635b15e44346b8b0f997bacad10b
Source dataset
uspto-grants-2006_06
Patent number
US07057036B2

Reaction notes

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