Water → HCID 13060477, compound

HRID 1719931Notes

Reaction equation

HRID 1719931 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.C(O[CH:17]=[C:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20])C.O>CN(C)C=O>[CH2:22]([O:21][C:19](=[O:20])[C:18](=[CH:17][NH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1)[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:23]

Participants

5

Reactant 3

HCID 962WaterHCID 6871Diethyl (ethoxymethylene)malonateHCID 13060446HCID 13060446, compound

Product 1

HCID 13060477HCID 13060477, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4-amino-6-ethylquinazoline (6.35 g) and diethyl ethoxymethylenepropanedioate (9.52 g) in N,N-dimethylformamide (25 ml) was stirred for 3 hours at 110° C. and then cooled to ambient temperature. A small volume of water was added to the resultant mixture to precipitate crystals, which were separated by filtration and washed with water. The crystals were dissolved in chloroform, washed with an aqueous solution saturated with sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a crystalline residue, which was recrystallized from a mixture of ethyl acetate and hexane to give crystalline diethyl[(6-ethyl-4-quinazolinylamino)methylene]propanedioate (8.40 g). Further, crystals (2.75 g) of the same compound were recovered from the motor liquor in the same manner as mentioned above.

Workup

  1. temperaturecooled to ambient temperature
  2. customto precipitate crystals, which
  3. customwere separated by filtration
  4. washwashed with water
  5. dissolutionThe crystals were dissolved in chloroform
  6. washwashed with an aqueous solution saturated with sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto give a crystalline residue, which
  10. customwas recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-3df6f773a2d94aafa691e5b2f0a07646
Source dataset
uspto-grants-1985_09
Patent number
US04543356

Reaction notes

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