503856-72-2

Basic information

• Product Name: 3-(3-chloropropyl)-2-phenylquinazolin-4(3H)-one
• Synonyms: 3-(3-chloropropyl)-2-phenylquinazolin-4(3H)-one
• CAS NO: 503856-72-2
• Molecular Weight: 298.772
• Mol File: 503856-72-2.mol

Chemical Properties

• CAS DataBase Reference: 3-(3-chloropropyl)-2-phenylquinazolin-4(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(3-chloropropyl)-2-phenylquinazolin-4(3H)-one(503856-72-2)
• EPA Substance Registry System: 3-(3-chloropropyl)-2-phenylquinazolin-4(3H)-one(503856-72-2)

Safety Data

• Hazardous Substances Data: 503856-72-2(Hazardous Substances Data)

Upstream product

• 1022-45-3 2-phenyl-4(3H)-quinazolinone 
• 109-70-6 1.3-chlorobromopropane 
• 503856-77-7 4-(3-chloropropoxy)-2-phenylquinazoline 
• 98-88-4 benzoyl chloride 
• 93-97-0 benzoic acid anhydride 
• 28144-70-9 anthranilic acid amide 

Relevant articles and documents

Lewis-acid-promoted cyclization reaction: Synthesis of N3-chloroethyl and N3-thiocyanatoethyl quinazolinones

A Lewis-acid-promoted cyclization reaction of benzoyl chlorides with 2-(4,5-dihydrooxazol-2-yl)anilines, which can offer a series of N3-chloroethyl quinazolinones, is disclosed. The reaction is compatible with the functional groups of the substrates; environment-friendly AlCl3 is probably the chloride source. Moreover, the addition of NH4SCN can also produce a range of N3-thiocyanatoethyl quinazolinones in moderate-to-good yields.

Studies on quinazolines. 11. Intramolecular imidate-amide rearrangement of 2-substituted 4-(ω-chloroalkoxy)quinazoline derivatives. 1,3 -O → N shift of chloroalkyl groups via cyclic 1,3-azaoxonium intermediates

The ω-chloroalkylation of 2-substituted quinazo lin-4(3H)-one derivatives 1 and 2 with Br-(CH2)n-Cl (n = 2-4) and the intramolecular imidate-amide rearrangement of the alkylated products are described. At room temperature, the 2-phenyl substituent promoted O-alkylation, whereas the less steric 2-benzyl group led to a higher ratio of N-alkylation. The investigation of the O-alkylated products, 4-ω-chloroalkoxyquinazolines, revealed that the migration of ω-chloroethyl and ω-chloropropyl groups from oxygen to nitrogen should be intramolecular via five- and six-membered cyclic 1,3-azaoxonium intermediates, respectively. Competition between rearrangement and nucleophilic substitution results in the formation of 7a,b and 8a,b from the nucleophilic substitution of 4a,b and 6a,b, respectively.