Isopropanol → HCID 86737898, compound

HRID 1278359Notes

Reaction equation

HRID 1278359 reaction equation
C(C1C=C2C(=C(C(C)C)C=1)N=CN(/[CH:17]=[CH:18]/[C:19]([OH:21])=[O:20])C2=O)(C)C.[CH2:23]([N:25]([CH2:29][CH3:30])[CH2:26][CH2:27]Cl)[CH3:24].C(O)(C)C.[C:35]([OH:42])(=[O:41])/[CH:36]=[CH:37]\[C:38]([OH:40])=[O:39]>CCOCC.C(Cl)Cl>[C:35]([OH:42])(=[O:41])/[CH:36]=[CH:37]\[C:38]([OH:40])=[O:39].[C:19]([O:21][CH2:27][CH2:26][N:25]([CH2:23][CH3:24])[CH2:29][CH3:30])(=[O:20])[CH:18]=[CH2:17]

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 13364Diethylaminoethyl chlorideHCID 444266Maleic AcidHCID 12881326HCID 12881326, compound

Product 1

HCID 86737898HCID 86737898, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 1.42 g. of trans-3-(6,8-diisopropyl-4-oxo-4H-quinazolin-3-yl)-2-propenoic acid and 1.36 g. of 2-(diethylamino)ethyl chloride in 150 ml. of isopropyl alcohol was stirred and heated at reflux for 16 hours. The reaction mixture was concentrated in vacuo and then partitioned between methylene chloride and saturated sodium bicarbonate solution. The methylene chloride layer was dried (sodium sulfate) and concentrated in vacuo to yield 1.20 g. of an oil. The oil was dissolved in 5 ml. of methylene chloride and treated with a solution of 0.35 g. of maleic acid in 25 ml. of ether. After concentration in vacuo, the residue was crystallized from isopropyl alcohol-ether to give trans-3-(6,8-diisopropyl-4-oxo-4H-quinazolin)-3-yl)-2-propenoic acid, 2-(diethylamino)ethyl ester maleate, mp 81°-83°.

Workup

  1. additionA suspension of 1.42 g
  2. temperatureheated
  3. temperatureat reflux for 16 hours
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. custompartitioned between methylene chloride and saturated sodium bicarbonate solution
  6. dry with materialThe methylene chloride layer was dried (sodium sulfate)
  7. concentrationconcentrated in vacuo
  8. customto yield 1.20 g
  9. dissolutionThe oil was dissolved in 5 ml
  10. concentrationAfter concentration in vacuo
  11. customthe residue was crystallized from isopropyl alcohol-ether

Sources & evidence

ORD record
ord-5633b491ebca4dfcafc9fb940b1b7feb
Source dataset
uspto-grants-1981_07
Patent number
US04281127

Reaction notes

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