Acetic Acid → 4(3H)-Quinazolinone, 2-ethyl-3-(phenylmethyl)-

HRID 1827311Notes

Reaction equation

HRID 1827311 reaction equation
[C:1]([CH:9]([NH:11][C:12](=[O:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH:19][CH:20]=O)C)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4]C=1.[Br:23]Br.[C:25](O)(=O)[CH3:26]>>[CH2:25]([C:20]1[N:11]([CH2:9][C:1]2[CH:2]=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:12](=[O:22])[C:13]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:19]=1)[CH3:26].[Br:23][CH:25]([C:20]1[N:11]([CH2:9][C:1]2[CH:2]=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:12](=[O:22])[C:13]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:19]=1)[CH3:26]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24408BromineHCID 22137673HCID 22137673, compound3×

Product 2

HCID 8282554(3H)-Quinazolinone, 2-ethyl-3-(phenylmethyl)-HCID 4353710HCID 4353710, compound

Procedure

2-Ethyl-3-benzyl-quinazolin-4-one is prepared following the procedure set forth in part (A) above, but substituting N-benzyl-2-(propanoylamino)-benzamide for N-(1-benzoylethyl)-2-(formylamino)-benzamide (“Compound E”). Compound E is brominated by heating in acetic acid with bromine to provide 2-(1-bromoethyl)-3-benzyl-quinazolin-4-one (“Compound F”). Compound F is treated with 4-methoxy-aniline in triethylamine to provide 2-(1-(4-methoxyphenylamino)ethyl)-3-benzyl-quinazolin-4-one (“Compound G”). Compound G is then acylated with benzoyl chloride to provide 2-(1-(N-benzoyl-N-(4-methoxyphenyl)-aminoethyl)-3-benzyl-quinazolin-4-one.

Sources & evidence

ORD record
ord-d96da94880e1435daf02c9762020baec
Source dataset
uspto-grants-2006_05
Patent number
US07053216B2

Reaction notes

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