Water → Diethyl[(4-quinazolinylamino)methylene]propanedioate

HRID 354859

Reaction equation

HRID 354859 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.C(O[CH:15]=[C:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18])C.O>CN(C)C=O>[N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([NH:1][CH:15]=[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6871Diethyl (ethoxymethylene)malonateHCID 847594-Aminoquinazoline

Product 1

HCID 13060467Diethyl[(4-quinazolinylamino)methylene]propanedioateYield 90.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 4-aminoquinazoline (11.6 g) and diethyl ethoxymethylenepropanedioate (19.0 g) in N,N-dimethylformamide (40 ml) was stirred for 1 hour and 20 minutes at 160° C. and then cooled to 0° C. to precipirate crystals. To the mixture was added small volume of water with stirring. The crystals were separated by filtration, washed with water, dried overnight under reduced pressure and dissolved in ethyl acetate. The resultant solution was dried over anhydrous magnesium sulfate and recrystallized from a mixture of ethyl acetate and hexane to give crystalline diethyl [(4-quinazolinylamino)methylene]propanedioate (22.7 g).

Workup

  1. temperaturecooled to 0° C.
  2. stirringwith stirring
  3. customThe crystals were separated by filtration
  4. washwashed with water
  5. customdried overnight under reduced pressure
  6. dissolutiondissolved in ethyl acetate
  7. dry with materialThe resultant solution was dried over anhydrous magnesium sulfate
  8. customrecrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-a674ad12d829424a8e074743555aae8c
Source dataset
uspto-grants-1983_03
Patent number
US04377580

Linked notes

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