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

HRID 1176205Notes

Reaction equation

HRID 1176205 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-ed9ea226cd91485589dd5e0a586e29fe
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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