Acetyl chloride → 3-(4-Methoxyphenyl)-5,6-dihydro-6-acetylimidazo[1,5-c]-quinazoline

HRID 481953Notes

Reaction equation

HRID 481953 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]3[CH2:14][NH:15][C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=4[C:12]3=[CH:11][N:10]=2)=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[C:31](Cl)(=[O:33])[CH3:32]>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]3[CH2:14][N:15]([C:31](=[O:33])[CH3:32])[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=4[C:12]3=[CH:11][N:10]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 154787163-(4-Methoxyphenyl)-5,6-dihydroimidazo[1,5-c]quinazoline

Product 1

HCID 216972203-(4-Methoxyphenyl)-5,6-dihydro-6-acetylimidazo[1,5-c]-quinazoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-(4-methoxyphenyl)-5,6-dihydroimidazo[1,5-c]quinazoline (100 mg) and diisopropylethylamine (50 ml) in THF (20 ml) is added acetyl chloride (50 ml) and the mixture stirred at RT for 5 hours. The reaction is extracted with ethyl acetate (200 ml), the solvent evaporated, and the residue is purified by preparative-plate chromatography (75% ethyl acetate/hexane) to afford 3-(4-methoxyphenyl)-5,6-dihydro-6-acetylimidazo[1,5-c]-quinazoline (Compound 49) as a light yellow solid. m.p. 80°-82° C.

Workup

  1. extractionThe reaction is extracted with ethyl acetate (200 ml)
  2. customthe solvent evaporated
  3. customthe residue is purified by preparative-plate chromatography (75% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-acda0d2d1a274facb134502a64838c93
Source dataset
uspto-grants-1998_08
Patent number
US05792766

Reaction notes

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