Potassium Iodide → 6-Hydroxymethyl-4-(3-methoxypropyl)-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one

HRID 1176633Notes

Reaction equation

HRID 1176633 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[C:9](=[O:14])[NH:8][C:7]=2[CH:15]=1.Cl[CH2:17][CH2:18][CH2:19][O:20][CH3:21].[F-].[K+].[I-].[K+]>C(#N)C>[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[C:9](=[O:14])[N:8]([CH2:17][CH2:18][CH2:19][O:20][CH3:21])[C:7]=2[CH:15]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 1189271-Chloro-3-methoxypropaneHCID 522689Potassium FluorideHCID 685012366-hydroxymethyl-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 675429806-Hydroxymethyl-4-(3-methoxypropyl)-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 2.270 g of 6-hydroxymethyl-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one in 180 ml of acetonitrile is admixed with 2.410 ml of 1-chloro-3-methoxypropane, 9.844 g of potassium fluoride on alumina and 0.036 g of potassium iodide. The reaction mixture is heated to reflux over 30 hours and filtered through Hyflo, and the filtrate is concentrated. The title compound is obtained as a beige solid from the residue by means of flash chromatography (SiO2 60F). Rf=0.20 (3:1 EtOAc-heptane); Rt=3.25.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux over 30 hours
  3. filtrationfiltered through Hyflo
  4. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-84b396882021486097c97e303b63caf4
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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