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

HRID 1712243Notes

Reaction equation

HRID 1712243 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][C:9](=[O:12])[NH:8][C:7]=2[CH:13]=1.Cl[CH2:15][CH2:16][CH2:17][O:18][CH3:19].[F-].[K+].[I-].[K+]>C(#N)C>[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][C:9](=[O:12])[N:8]([CH2:15][CH2:16][CH2:17][O:18][CH3:19])[C:7]=2[CH:13]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 1189271-Chloro-3-methoxypropaneHCID 522689Potassium FluorideHCID 184524436-(Hydroxymethyl)-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 534011966-Hydroxymethyl-4-(3-methoxypropyl)-4H-benzo[1,4]oxazin-3-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The suspension of 1.79 g of 6-hydroxymethyl-4H-benzo[1,4]oxazin-3-one, 2.20 ml of 1-chloro-3-methoxypropane, 10 g of KF on alumina and 0.033 g of potassium iodide in 150 ml of acetonitrile is stirred at reflux over 72 hours. The reaction mixture is cooled and clarified by filtration, and the filtrate is concentrated by evaporation to dryness. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F). Rf=0.60 (9:1 dichloromethane-methanol); Rt=2.74.

Workup

  1. temperatureat reflux over 72 hours
  2. temperatureThe reaction mixture is cooled
  3. filtrationclarified by filtration
  4. concentrationthe filtrate is concentrated by evaporation to dryness

Sources & evidence

ORD record
ord-047f45666a9a4055b6aef6a85dc55819
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Reaction notes

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