18046-21-4

Basic information

• Product Name: FENTIAZAC
• Synonyms: 4-(4-chlorophenyl)-2-phenyl-5-thiazoleaceticacid;4-(p-chlorophenyl)-2-phenyl-5-thiazoleaceticaci;4-(p-chlorophenyl)-2-phenyl-5-thiazoleaceticacid;4-(p-chlorophenyl)-2-phenylthiazole-5-aceticacid;br700;ch800;donorest;4-(4-chlorophenyl)-2-phenyl-5-thiazoleaceticaci
• CAS NO: 18046-21-4
• Molecular Formula: C₁₇H₁₂ClNO₂S
• Molecular Weight: 329.8
• EINECS: 241-958-1
• Mol File: 18046-21-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 162°C
• Boiling Point: 556.2°Cat760mmHg
• Flash Point: 290.2°C
• Appearance: /
• Density: 1.1592 (rough estimate)
• Vapor Pressure: 3.3E-13mmHg at 25°C
• Refractive Index: 1.6100 (estimate)
• PKA: 3.89±0.10(Predicted)
• Water Solubility: 31.66mg/L(25 oC)
• CAS DataBase Reference: FENTIAZAC(CAS DataBase Reference)
• NIST Chemistry Reference: FENTIAZAC(18046-21-4)
• EPA Substance Registry System: FENTIAZAC(18046-21-4)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 18046-21-4(Hazardous Substances Data)

Usage

Originator

Norvedan,LPB,Italy,1975

Uses

Anti-inflammatory.

Manufacturing Process

13.6 g methyl 3-(p-chlorobenzoyl)-3-bromopropionate in 30 ml methanol are added to a solution of 5.6 g potassium thioacetate in 30 ml methanol. Immediate precipitation of KBr is observed. The suspension is refluxed for 10 minutes.It is cooled to ambient temperature, filtered, and the methanol is evaporated to dryness. 13.2 g methyl 3-(p-chlorobenzoyl)-3-thioacetylpropionate in the form of a chromatographically pure orange-colored oil are obtained.A suspension of 13.2 g methyl 3-(p-chlorobenzoyl)-3-thioacetylpropionate is agitated in 500 ml of a 2 N aqueous solution of KOH for 6 hours at ambient temperature in an atmosphere of nitrogen, followed by extraction with ethyl ether. The aqueous phase, adjusted to a pH equal to 2 with 2N HCl, is extracted with ethyl ether which was washed with water, dried over Na2SO4, and finally evaporated to dryness9.8 g of crude 3-(p-chlorobenzoyl)-3-mercaptopropionic acid are obtained. By recrystallizing from isopropyl ether there are obtained 8.6 g of pure product, MP 96°C to 97°C (yield: 79%).1.7 ml benzonitrile and 5.05 ml diethylamine are added to a solution of 4 g 3- (p-chlorobenzoyl)-3-thiol-propionic acid in 50 ml ethanol. The solution is agitated at ambient temperature for 60 minutes in an atmosphere of nitrogen. It is then evaporated to a syrupy consistency and 60 ml 50% aqueous acetic acid are added, whereupon the mixture is refluxed for 60 minutes. It is evaporated to a small volume, adjusted to a pH equal to 8 with a saturated solution of sodium bicarbonate and then extracted with ethyl ether. The aqueous phase is acidified with 2N HCl (Congo red), and then again extracted with ethyl ether. It is dried over Na2SO4 and evaporated to dryness. The evaporation residue is recrystallized from benzene and 4 g 4-(p-chlorophenyl)- 2-phenyl-thiazol-5-yl-acetic acid are obtained (MP = 152°C to 154°C, yield - 74.3%).

Therapeutic Function

Analgesic, Antipyretic, Antiinflammatory

InChI:InChI=1/C17H12ClNO2S/c18-13-8-6-11(7-9-13)16-14(10-15(20)21)22-17(19-16)12-4-2-1-3-5-12/h1-9H,10H2,(H,20,21)

Upstream product

• 35158-39-5 3-bromo-3-(4-chlorobenzoyl)propionic acid 
• 2227-79-4 benzenecarbothioamide 
• 1073-67-2 4-vinylbenzyl chloride 
• 122395-24-8 4-(4′-chlorophenyl)-2-phenylthiazole 
• 79-11-8 chloroacetic acid 
• 53715-67-6 5-bromo-2-phenyl-1,3-thiazole 
• 637-87-6 1-Chloro-4-iodobenzene 

Downstream Products

• 23821-96-7 2-[4-(4-chloro-phenyl)-2-phenyl-thiazol-5-yl]-acetamide 
• 53515-07-4 [4-(4-chloro-phenyl)-2-phenyl-thiazol-5-yl]-acetic acid butyl ester 
• 53515-27-8 [4-(4-chloro-phenyl)-2-phenyl-thiazol-5-yl]-acetonitrile 
• 244269-07-6 (CH₃)3Sn(C₁₇H₁₁ClNO₂S)*H₂O 

Relevant articles and documents

“Snapshot” Trapping of Multiple Transient Azolyllithiums in Batch

Recent developments in flow microreactor technology have allowed the use of transient organolithium compounds that cannot be realized in a batch reactor. However, trapping the transient aryllithiums in a “halogen dance” is still challenging. Herein is reported the trapping of such short-lived azolyllithiums in a batch reactor by developing a finely tuned in situ zincation using zinc halide diamine complexes. The reaction rate is controlled by the appropriate choice of diamine ligand. The reaction is operationally simple and can be performed at 0 °C with high reproducibility on a multigram scale. This method was applicable to a wide range of brominated azoles allowing deprotonative functionalization, which was used for the concise divergent syntheses of both constitutional isomers of biologically active azoles.

Novel selective thiazoleacetic acids as CRTH2 antagonists developed from in silico derived hits. Part 1

Structure-activity relationships of three related series of 4-phenylthiazol-5-ylacetic acids, derived from two hits emanating from a focused library obtained by in silico screening, have been explored as CRTH2 (chemoattractant receptor-homologous molecule expressed on Th2 cells) antagonists. Several compounds with double digit nanomolar binding affinity and full antagonistic efficacy for human CRTH2 receptor were obtained in all subclasses. The most potent compound was [2-(4-chloro-benzyl)-4-(4-phenoxy-phenyl)-thiazol-5-yl]acetic acid having an binding affinity of 3.7 nM and functional antagonistic effect of 66 nM in a BRET and 12 nM in a cAMP assay with no functional activity for the other PGD2 DP receptor (27 μM in cAMP).

Derivatives of antiphlogistically effective carboxylic acids, their preparation and medicinal use

Compounds of Formula I STR1 wherein R1 is the residue of an antiphlogistically effective carboxylic acid of the formula R1 COOH, n is an integer 1, 2, or 3, and X is oxygen, sulfur, or optionally alkylated nitrogen have valuable antiinflammatory activity.