Ammonium Acetate → 6,7-Bis(2-methoxyethoxy)quinazolin-4(1H)-one

HRID 1094538Notes

Reaction equation

[NH2:1][C:2]1[CH:12]=[C:11]([O:13][CH2:14][CH2:15][O:16][CH3:17])[C:10]([O:18][CH2:19][CH2:20][O:21][CH3:22])=[CH:9][C:3]=1[C:4](OCC)=[O:5].[CH:23]([O-])([O-])OC.C([O-])(=O)C.[NH4+:32]>CO>[CH3:22][O:21][CH2:20][CH2:19][O:18][C:10]1[CH:9]=[C:3]2[C:2](=[CH:12][C:11]=1[O:13][CH2:14][CH2:15][O:16][CH3:17])[N:1]=[CH:23][NH:32][C:4]2=[O:5]

Participants

Conditions

Temperature: 60 °C

Procedure

In a 20 L-volume glass reaction vessel equipped with a stirrer, a thermometer and a reflux condenser, 1,600 g (5.11 moles) of the ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate prepared in the Synthesis Example 3, 1,626 g (15.3 moles) of methyl orthoformate, 1,181 g (15.3 moles) of ammonium acetate and 4,800 mL of methanol were placed. The mixture was allowed to react under refluxing conditions (60 to 70° C.) for 7 hours while stirring. After the reaction was complete, the reaction solution was cooled to 60° C. To the reaction solution, 4,800 mL of methanol was added. The mixture was stirred for 30 minutes while maintaining the temperature, cooled to 0 to 5° C., and further stirred for 1 hour. The resulting mixture was filtered to obtain 1,373 g of 6,7-bis(2-methoxyethoxy)quinazolin-4-one as white crystals (isolation yield: 91%).

Workup

customIn a 20 L-volume glass reaction vessel
customequipped with a stirrer
customto react under refluxing conditions (60 to 70° C.) for 7 hours
stirringThe mixture was stirred for 30 minutes
temperaturewhile maintaining the temperature
temperaturecooled to 0 to 5° C.
stirringfurther stirred for 1 hour
filtrationThe resulting mixture was filtered

Sources & evidence

ORD record: ord-f1027bb32dbf48a0ba74e989aa59a4c4
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08133999B2

Reaction notes

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