Hexane → HCID 15289933, compound

HRID 1975706Notes

Reaction equation

HRID 1975706 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[CH2:4][C:5]1[O:10][CH2:9][CH2:8][O:7][N:6]=1.[Br:15]N1C(=O)CCC1=O.C(OCC)(=O)C.CCCCCC>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[CH:4]([Br:15])[C:5]1[O:10][CH2:9][CH2:8][O:7][N:6]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 14879552HCID 14879552, compound

Product 1

HCID 15289933HCID 15289933, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

4.0 g (19 mmole) of 3-(2-chlorobenzyl)-5,6-dihydro-1,4,2-dioxazine (prepared as described in Preparation 1) were dissolved in 40 ml of carbon tetrachloride, and then 4.1 g (23 mmole) of N-bromosuccinimide and 0.2 g of benzoyl peroxide were added to the solution, which was then stirred, whilst heating, for 8 hours. At the end of this time, 100 ml of ethyl acetate and 100 ml of hexane were added to the solution, and the mixture was stirred at room temperature for 30 minutes; insolubles were then removed by filtration. The filtrate was concentrated by evaporation under reduced pressure, to give 4.8 g of the title compound as a yellow oil.

Workup

  1. temperaturewhilst heating, for 8 hours
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. custominsolubles were then removed by filtration
  4. concentrationThe filtrate was concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-db1856477e9e4c9ba559e754190def51
Source dataset
uspto-grants-1994_02
Patent number
US05288726

Reaction notes

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