2-Methoxyethanol → HCID 18980323, compound

HRID 1900675Notes

Reaction equation

HRID 1900675 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][OH:5].[H-].[Na+].Cl[C:9]1[N:18]=[C:17]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]3[O:27][CH2:28][O:29][C:23]=3[CH:22]=2)[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:30])[CH:15]=2)[N:10]=1>O>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:9]1[N:18]=[C:17]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]3[O:27][CH2:28][O:29][C:23]=3[CH:22]=2)[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:30])[CH:15]=2)[N:10]=1

Participants

5

Reactant 3

HCID 80192-Methoxyethanol2×HCID 24758Sodium hydrideHCID 223398654-((1,3-Benzodioxol-5-ylmethyl)amino)-2,6-dichloro quinazoline

Product 1

HCID 18980323HCID 18980323, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture comprising 20 ml of ethylene glycol monomethyl ether and 70 mg of 55% sodium hydride was heated to 100° C., followed by the addition of a mixture comprising 500 mg of 2,6-dichloro-4-(3,4-methylenedioxybenzyl)aminoquinazoline and 5 ml of ethylene glycol monomethyl ether. The obtained mixture was heated under reflux for 2 hours and poured into 50 ml of water. The obtained mixture was extracted with 50 ml of ethyl acetate twice. The organic layers were together washed with 70 ml of an aqueous solution of sodium chloride twice, dried over magnesium sulfate and concentrated under a reduced pressure to give a crystalline residue. This residue was reprecipitated from ethyl acetate/n-hexane to give 420 mg of the title compound.

Workup

  1. temperatureThe obtained mixture was heated
  2. temperatureunder reflux for 2 hours
  3. extractionThe obtained mixture was extracted with 50 ml of ethyl acetate twice
  4. washThe organic layers were together washed with 70 ml of an aqueous solution of sodium chloride twice
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under a reduced pressure
  7. customto give a crystalline residue
  8. customThis residue was reprecipitated from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-686c076afa34448f89f0b1fbabc47e83
Source dataset
uspto-grants-1996_11
Patent number
US05576322

Reaction notes

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