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

HRID 2246909Notes

Reaction equation

HRID 2246909 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

A stirred suspension of 1.79 g of 6-hydroxymethyl-4H-benzo[1,4]oxazin-3-one, 2.20 ml of 1-chlor-3-methoxypropane, 10 g of potassium fluoride on aluminium oxide and 0.033 g potassium iodide in 150 ml of acetonitrile is heated to reflux for 72 hours. The reaction mixture is allowed to cool to room temperature, filtered and concentrated under reduced pressure. The residue is purified by flash chromatography (SiO2 60 F) to afford the title compound. Rf=0.60 (dichlormethane-methanol 9:1); Rt=2.74.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 72 hours
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-6bed7fb5614b44d383bb869626dc1b8e
Source dataset
uspto-grants-2010_03
Patent number
US07687495B2

Reaction notes

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