Potassium Carbonate → HCID 12881313, compound

HRID 745513Notes

Reaction equation

HRID 745513 reaction equation
[CH3:1][CH:2]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([CH:14]([CH3:16])[CH3:15])[CH:13]=1)[N:10]=[CH:9][NH:8][C:7]2=[O:17])[CH3:3].[CH3:18][O:19][C:20](=[O:24])/[CH:21]=[CH:22]\Cl.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:18][O:19][C:20](=[O:24])/[CH:21]=[CH:22]/[N:8]1[C:7](=[O:17])[C:6]2[C:11](=[C:12]([CH:14]([CH3:16])[CH3:15])[CH:13]=[C:4]([CH:2]([CH3:1])[CH3:3])[CH:5]=2)[N:10]=[CH:9]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 53522742-Propenoic acid, 3-chloro-, methyl ester, (2Z)-HCID 136147100HCID 136147100, compound

Product 1

HCID 12881313HCID 12881313, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3.10 g (0.013)mol) of 6,8-bis-(1-methylethyl)-quinazolin-4(3H)-one, 1.78 g (0.0148 mol) of (Z)-3-chloro-2-propenoic acid methyl ester and 3.72 g (0.027 mol) of anhydrous potassium carbonate in 100 ml. of anhydrous acetone was stirred at reflux for 17 hr. The reaction mixture was filtered, the solid was washed with acetone and the filtrate was concentrated in vacuo to an oil which soon crystallized. Recrystallization from methanol gave 3.11 g, m.p. 102°-103°, (74% yield) of (E)-3-[6,8-bis-(1-methylethyl)-4-oxo-4H-quinazolin-3-yl]-2-propenoic acid methyl ester.

Workup

  1. temperatureat reflux for 17 hr
  2. filtrationThe reaction mixture was filtered
  3. washthe solid was washed with acetone
  4. concentrationthe filtrate was concentrated in vacuo to an oil which
  5. customsoon crystallized
  6. customRecrystallization from methanol

Sources & evidence

ORD record
ord-cb2139f2827641c5b8f726687c09c2b6
Source dataset
uspto-grants-1986_07
Patent number
US04599336

Reaction notes

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