21721-78-8

Basic information

• Product Name: 2-(2-CHLORO-ACETYLAMINO)-BENZAMIDE
• Synonyms: 2-(2-CHLORO-ACETYLAMINO)-BENZAMIDE;2-[(CHLOROACETYL)AMINO]BENZAMIDE;AKOS BBS-00006956;AKOS B015655;CHEMBRDG-BB 3015655;ART-CHEM-BB B015655;2-[(chloroacetyl)amino]benzamide(SALTDATA: FREE);2'-CARBAMOYL-2-CHLOROACETANILIDE
• CAS NO: 21721-78-8
• Molecular Formula: C₉H₉ClN₂O₂
• Molecular Weight: 212.63
• Mol File: 21721-78-8.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 467.2 °C at 760 mmHg
• Flash Point: 236.4 °C
• Appearance: /
• Density: 1.393 g/cm³
• Vapor Pressure: 6.62E-09mmHg at 25°C
• Refractive Index: 1.63
• CAS DataBase Reference: 2-(2-CHLORO-ACETYLAMINO)-BENZAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-CHLORO-ACETYLAMINO)-BENZAMIDE(21721-78-8)
• EPA Substance Registry System: 2-(2-CHLORO-ACETYLAMINO)-BENZAMIDE(21721-78-8)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 21721-78-8(Hazardous Substances Data)

Usage

General Description

2-(2-chloro-acetylamino)-benzamide is a chemical compound with the molecular formula C9H8ClNO2. It is a white to off-white crystalline powder that is soluble in organic solvents such as methanol, ethanol, and dimethylsulfoxide. 2-(2-CHLORO-ACETYLAMINO)-BENZAMIDE is commonly used in pharmaceutical research as a building block for the synthesis of various bioactive molecules. It is also known for its potential antitumor and antimicrobial activities. In addition, 2-(2-chloro-acetylamino)-benzamide is used as an intermediate in the production of other chemicals and pharmaceuticals. Due to its diverse applications, this compound is of interest to researchers and scientists in the fields of medicine, chemistry, and pharmaceuticals.

InChI:InChI=1/C9H9ClN2O2/c10-5-8(13)12-7-4-2-1-3-6(7)9(11)14/h1-4H,5H2,(H2,11,14)(H,12,13)

Upstream product

• 610-15-1 2-nitrobenzamide 
• 28144-70-9 anthranilic acid amide 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 827010-09-3 2-[2-(4-oxo-3,4-dihydroquinazolin-2-ylsulfanyl)acetylamino]benzamide 
• 199114-62-0 2-chloromethyl-3-methyl-4-oxo-3,4-dihydroquinazoline 
• 1004413-14-2 2-(2-(2,4-dioxothiazolidin-3-yl)acetamido)benzamide 
• 1345089-69-1 2-(2-((E)-5-(2-chlorobenzylidene)-2,4-dioxothiazolidin-3-yl)acetamido)benzamide 
• 1345089-68-0 2-(2-((E)-5-benzylidene-2,4-dioxothiazolidin-3-yl)acetamido)benzamide 
• 1345089-67-9 2-(2-((5E)-2,4-dioxo-5-((E)-3-phenylallylidene)thiazolidin-3-yl)acetamido)benzamide 
• 1345089-66-8 2-(2-((E)-5-(2-hydroxybenzylidene)-2,4-dioxothiazolidin-3-yl)acetamido)benzamide 
• 1345089-65-7 2-(2-((E)-5-(4-methoxybenzylidene)-2,4-dioxothiazolidin-3-yl)acetamido)benzamide 
• 1345089-64-6 2-(2-((E)-5-(4-hydroxy-3-methoxybenzylidene)-2,4-dioxothiazolidin-3-yl)acetamido)benzamide 
• 1345089-63-5 2-(2-((E)-5-(4-(benzyloxy)-3-methoxybenzylidene)-2,4-dioxothiazolidin-3-yl)acetamido)benzamide 
• 1345089-62-4 2-(2-((E)-5-(4-(dimethylamino)benzylidene)-2,4-dioxothiazolidin-3-yl)acetamido)benzamide 
• 1345089-61-3 2-(2-((E)-5-(4-hydroxybenzylidene)-2,4-dioxothiazolidin-3-yl)acetamido)benzamide 
• 1273022-06-2 2-{[4-(4-nitrophenyl)piperazin-1-yl]methyl}quinazolin-4(3H)-one 
• 896665-78-4 2-{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}quinazolin-4(3H)-one 

Relevant articles and documents

Synthesis and evaluation of anticancer and PDE 5 inhibitory activity of spiro-substituted quinazolin-4-ones

A series of novel spiro-substituted 2,3-dihydroquinazolin-4(1H)-ones was synthesized and structurally confirmed by spectral analysis, screened for their anticancer activity at a concentration of 10 μΜ against a panel of 56 cell lines derived from nine different types of cancers, including leukemia, melanoma, lung, colon, CNS, ovarian, renal, prostate, and breast cancers. The synthesized compounds screened for their PDE 5 inhibitory activity and it showed encouraged activity compared to sildenafil. Graphical abstract: [Figure not available: see fulltext.].

Synthesis of benzoxazolthiolyl and benzthiazolthiolyl fused 3- alkylquinazolin-4(3H)-ones

Condensation of anthranilamide (1) with chloroacetyl chloride for 1 hr at RT gave 2- (2-chloroacetamido) benzamide (2). The latter, on refluxation in acetic acid for 2 hr gave 2-(chloromethyl) quinazolin-4(3H)-one (3). Condensation of 3, independently, with each one of benz [d] oxazole-2-thiol (4a) and benz [d] thiazole-2-thiol (4b), for 3-4 hr, gave 2-((benz [d] oxazol-2-ylthio) methyl) quinazolin-4(3H)-one (5a) and 2-((benz [d] thiazol-2-ylthio) methyl) quinazolin-4(3H)-one (5b) respectively. Each one of the 5a and 5b, independently and selectively, when treated with alkylating agents (i.e. DMS, DES, PhCH2Cl), gave 2-((benz [d] oxazol-2-ylthio) methyl)-3-alkylquinazolin-4(3H)-ones (6a-c) and 2-((benz [d] thiazol-2-ylthio) methyl)-3-alkylquinazolin-4(3H)-ones (6d-f) respectively. The latter 6a-f could also be prepared, alternatively, by condensing chloromethyl-3-alkylquinazolin-4(3H)-one (7a-c) with 4a-b respectively, in good yields.

Synthesis of novel 2-(4-oxo-3,4-dihydroquinazolin-2-ylsulfinylmethyl)-3H- quinazolin-4-one

Condensation of 2-mercapto-3H-quinazolin-4-one (1) with chloroacetic acid gave 4-oxo-3,4-dihydroquinazoline-2-yl-sulfanyl)-acetic acid (2) that with anthranilamide (3) gave 2-(4-oxo-3,4-dihydroquinazolin-2-ylsulfanylmethyl)-3H- quinazolin-4-one (4). Oxidation of 4 with sodium hypochlorite in alkaline medium gave the novel product, 2-(4-oxo-3,4-dihydroquinazolin-2-ylsulfinyl methyl)-3H-quinazolin-4-one) (5). The entire sequences of reactions in this work have been carried out using eco-friendly solvents and green conditions. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.