Potassium Iodide → 6-bromo-4-(3-methoxypropyl)-4H-benzo[1,4]oxazin-3-one

HRID 252359

Reaction equation

HRID 252359 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=2[CH:12]=1.Cl[CH2:14][CH2:15][CH2:16][O:17][CH3:18].[F-].[K+].[I-].[K+]>C(#N)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C:8](=[O:11])[N:7]([CH2:14][CH2:15][CH2:16][O:17][CH3:18])[C:6]=2[CH:12]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 1189271-Chloro-3-methoxypropaneHCID 522689Potassium FluorideHCID 162181426-Bromo-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 231485196-bromo-4-(3-methoxypropyl)-4H-benzo[1,4]oxazin-3-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

The suspension of 9.87 g of 6-bromo-4H-benzo[1,4]oxazin-3-one [24036-52-0], 9.40 g of 1-chloro-3-methoxypropane, potassium fluoride on alumina (Fluka 60244), 0.144 g of potassium iodide in 500 ml of acetonitrile is stirred at 100° C. over 40 hours. The reaction mixture is cooled to room temperature and filtered through Hyflo, and the filtrate is concentrated by evaporation to dryness. The title compound is obtained as a slightly yellowish solid from the residue by crystallization from ethyl acetate. Rf=0.43 (1:1 EtOAc-heptane). Rt=4.27 (gradient I). m.p. 193-195° C.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. filtrationfiltered through Hyflo
  3. concentrationthe filtrate is concentrated by evaporation to dryness

Sources & evidence

ORD record
ord-658a8b47ad394f8fa6693bdf46507888
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Linked notes

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