1-Bromo-2-Chloroethane → HCID 15542506, compound

HRID 635179Notes

Reaction equation

HRID 635179 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH:10]=[CH:9][NH:8][C:7](=[O:12])[C:6]=2[CH:13]=1.[H-].[Na+].Br[CH2:17][CH2:18][Cl:19].C(OCC)(=O)C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH:10]=[CH:9][N:8]([CH2:17][CH2:18][Cl:19])[C:7](=[O:12])[C:6]=2[CH:13]=1

Participants

6

Reactant 4

HCID 78491-Bromo-2-ChloroethaneHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 15542509HCID 15542509, compound

Product 1

HCID 15542506HCID 15542506, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50 mg of 7-chloro-4,5-dihydro-1,4-benzoxazepin-5-one was dissolved in dimethylformamide (1 ml), then 12 mg (1.2 equivalents) of 60% sodium hydride was added under ice cooling. This was agitated for 30 minutes, then 54 mg (1.5 equivalents) of 1-bromo-2-chloroethane was added and the result was agitated at room temperature for 10 hours. Ice water was added to the reaction solution, and extraction was performed by ethyl acetate. This ethyl acetate extract was washed by saline and was dried with anhydrous magnesium sulfate. The solvent was distilled off and the resultant crude product was refined with silica gel column chromatography (hexane:ethyl acetate 4:1) to obtain the above-referenced compound in an amount. of 28 mg (yield of 42%).

Workup

  1. stirringthe result was agitated at room temperature for 10 hours
  2. extractionThis ethyl acetate extract
  3. washwas washed by saline
  4. dry with materialwas dried with anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customto obtain the above-referenced compound in an amount

Sources & evidence

ORD record
ord-76c2627dafd94887a89898c11eb5a282
Source dataset
uspto-grants-2001_02
Patent number
US06187769B1

Reaction notes

Loading…