30544-61-7

Basic information

• Product Name: clanobutin
• Synonyms: clanobutin;4-[(4-Chlorobenzoyl)(4-methoxyphenyl)amino]butanoic acid;4-[(4-Chlorobenzoyl)(4-methoxyphenyl)amino]butyric acid;4-[p-Chlorobenzoyl(p-methoxyphenyl)amino]butyric acid;B-6518;Clanobutin sodiuM;Butanoic acid,4-[(4-chlorobenzoyl)(4-Methoxyphenyl)aMino]-
• CAS NO: 30544-61-7
• Molecular Formula: C18H18ClNO4
• Molecular Weight: 347.7928
• EINECS: 250-232-3
• Mol File: 30544-61-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 115-116°
• Boiling Point: 562.4°Cat760mmHg
• Flash Point: 294°C
• Appearance: /
• Density: 1.1976 (rough estimate)
• Vapor Pressure: 1.73E-13mmHg at 25°C
• Refractive Index: 1.6800 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 5.04(at 25℃)
• Water Solubility: 44.17mg/L(37 oC)
• CAS DataBase Reference: clanobutin(CAS DataBase Reference)
• NIST Chemistry Reference: clanobutin(30544-61-7)
• EPA Substance Registry System: clanobutin(30544-61-7)

Safety Data

• Hazardous Substances Data: 30544-61-7(Hazardous Substances Data)

Usage

Uses

Clanobutin inhibits gluconeogenesis in isolated perfused rat livers. it is a a choleretic and digestion-stimulating agent for animals.

InChI:InChI=1/C18H18ClNO4/c1-24-16-10-8-15(9-11-16)20(12-2-3-17(21)22)18(23)13-4-6-14(19)7-5-13/h4-11H,2-3,12H2,1H3,(H,21,22)

Synthetic route

4-<4-chloro-N-(4-methoxyphenyl)-benzamido>-butyric acid (30544-61-7) + 4-[(2,6-dimethylphenyl)amino]butyric acid ethyl ester (71454-70-1) → N-[N-(p-chlorobenzoyl)-4-(p-anisidino)butyryl]-4-(2,6-dimethylanilino)-butyric acid (71455-67-9)

Conditions	Yield
(i) ClCO2Et, Et3N, (ii) /BRN= 2736307/, (iii) KOH; Multistep reaction;

4-<4-chloro-N-(4-methoxyphenyl)-benzamido>-butyric acid (30544-61-7) + γ-(p-Anisidino)-buttersaeureaethylester (51814-72-3) → N-[N-(p-chlorobenzoyl)-4-(p-anisidino)butyryl]-4-(p-anisidino)butyric acid (71454-78-9)

Conditions	Yield
(i) ClCO2Et, Et3N, (ii) /BRN= 2737185/, (iii) KOH; Multistep reaction;

4-<4-chloro-N-(4-methoxyphenyl)-benzamido>-butyric acid (30544-61-7) → ethyl N-[N-(p-chlorobenzoyl)-4-(p-anisidino)butyryl]-4-(2,6-dimethylanilino)butyrate + N-[N-(p-chlorobenzoyl)-4-(p-anisidino)butyryl]-4-(2,6-dimethylanilino)-butyric acid (71455-67-9)

4-<4-chloro-N-(4-methoxyphenyl)-benzamido>-butyric acid (30544-61-7) → N-[N-(p-chlorobenzoyl)-4-(p-anisidino)butyryl]-4-(p-anisidino)butyric acid (71454-78-9)

Conditions	Yield
With potassium hydroxide; thionyl chloride; diisopropylamine In methanol; ethanol; water; benzene

4-<4-chloro-N-(4-methoxyphenyl)-benzamido>-butyric acid (30544-61-7) → methyl N-[N-(p-chlorobenzoyl)-4-(p-anisidino)butyryl]-4-(p-anisidino)butyrate (71455-90-8) + N-[N-(p-chlorobenzoyl)-4-(p-anisidino)butyryl]-4-(p-anisidino)butyric acid (71454-78-9)

4-<4-chloro-N-(4-methoxyphenyl)-benzamido>-butyric acid (30544-61-7) → N-[N-(p-chlorobenzoyl)-4-(p-anisidino)butyryl]glycine (71489-33-3) + ethyl N-[N-(p-chlorobenzoyl)-4-(p-anisidino)butyryl]glycinate (71456-13-8)

Upstream product

• 149-74-6 dichloromethylphenylsilane 

Downstream Products

• 71489-33-3 N-[N-(p-chlorobenzoyl)-4-(p-anisidino)butyryl]glycine 
• 71456-13-8 ethyl N-[N-(p-chlorobenzoyl)-4-(p-anisidino)butyryl]glycinate 
• 71455-90-8 methyl N-[N-(p-chlorobenzoyl)-4-(p-anisidino)butyryl]-4-(p-anisidino)butyrate 
• 71454-78-9 N-[N-(p-chlorobenzoyl)-4-(p-anisidino)butyryl]-4-(p-anisidino)butyric acid 
• 71455-67-9 N-[N-(p-chlorobenzoyl)-4-(p-anisidino)butyryl]-4-(2,6-dimethylanilino)-butyric acid 

Relevant articles and documents

An ESR study on structures of a series of silylnitrenes

Structures of a series of silylnitrenes formed from silyl azides were investigated by means of ESR. γ-Irradiation and photo-illumination of all the silyl azides resulted in the formation of triplet states even for those having two or three Si-N3 groups in a molecule. ESR spectra of the silylnitrenes exhibited a part of the fine structure at around 820 mT. All the silyl azides studied gave nearly identical D-values (ca. 1.5cm-1) and much larger than those in phenylnitrenes. The results suggested that electron spins are localized in the nitrogen p-orbitals to a large extent and was interpreted in terms of a mono-silane linkage of nitrene, -Si-N:, i.e., interrupting spin delocalization.

Compositions of and new uses for N-acylanilinobutyric acids

Pharmaceutically-acceptable compositions containing, as an active ingredient, at least one N-acylanilinobutyric acid have uses unrelated to the choleretic activity suggested in U.S. Pat. No. 3,780,095. Moreover, the further uses generally involve administration of smaller doses than would be required to obtain a choleretic effect. The new uses include: a) increasing the gastrointestinal enzyme secretion and b) tonicizing the cardiovascular system. The increase of the gastrointestinal enzyme secretion is applied in the treatment of different diseases such as treatment of sprue, treatment of indigestion, treatment of acute and chronic pancreatitis, therapy for degenerated intestine mucous membrane, treatment of stomach spasms, treatment of stomach ulcers, treatment of diseases where the application of an antigastrin is indicated. The tonicizing of the cardiovascular system is applied in, e.g., increasing the circulation of blood in internal organs, increasing the heart force, reating disturbances in the liver function.