435-97-2 Usage
Chemical Properties
White Solid
Originator
Liquamar ,Organon ,US,1958
Uses
Phenprocoumon is known for being an oral anti-coagulant.
Definition
ChEBI: A hydroxycoumarin that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenylpropyl group.
Manufacturing Process
8.3 parts by weight of powdered sodium in 300 parts by volume of benzene, 100 parts by weight of diethyl (1'-phenylpropyl)-malonate and 72 parts by weight of acetylsalicylic acid chloride are reacted together to form diethyl 1(o-acetoxybenzoy1)-1-(1'-phenylpropyl)malonate, which boils at 195°198°C/0.03 mm Hg.10.3 parts of weight of diethyl 1-(o-acetoxybenzoyl)-1-(1'-phenylpropyl)malonate are dissolved in 60 parts by volume of absolute ether and to this solution are added portion. wise at 10°C, while stirring, 2.6 parts by weight of sodium methylate. The reaction mixture is stirred for 4 hours, whereupon it is poured into ice water. The ether solution is washed neutral with ice water. After having distilled off the ether, a thick oil consisting of 3-carbethoxy-3-(1'phenylpropyl)-4-oxo-dihydrocoumarinis obtained. This compound crystallized in butyl oxide and has a MP of 108°-109°C.The 3-carbethoxy-3-(1'-phenylpropyl)-4-oxo-dihydrocoumarinmay be hydrolyzed and decarboxylated as follows. The crude product is heated to 85°C for 1/2 hour with 100 parts by volume of 5% aqueous sodium hydroxide, while agitating or stirring. To remove traces of undissolved oil, the cooled solution is treated with 1 part by weight of charcoal, whereupon it is filtrated and acidified to Congo reaction with dilute sulfuric acid. The 3-(1'phenylpropyl)-4-hydroxycoumarin formed is separated off and recrystallized in 80% ethanol, whereupon it melts at 178°-179°C according to US Patent 2,701,804.
Brand name
Liquamar (Organon).
Therapeutic Function
Anticoagulant
Synthesis
Phenprocoumon, 3-(α-ethylbenzyl)-4-hydroxycoumarin (24.1.14), is
synthesized by acylating sodium salts of diethyl ester (1-phenylpropyl)butyric acid with
acetylsalicylic acid chloride, which forms the compound 24.1.12, which upon reaction
with sodium ethoxide cyclizes to 3-(α-ethylbenzyl)-2-carboethoxy-4-hydroxycoumarin
(24.1.13). Alkaline hydrolysis of this product and further decarboxylation gives phenprocoumon(24.1.14).
Check Digit Verification of cas no
The CAS Registry Mumber 435-97-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,3 and 5 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 435-97:
(5*4)+(4*3)+(3*5)+(2*9)+(1*7)=72
72 % 10 = 2
So 435-97-2 is a valid CAS Registry Number.
InChI:InChI=1/C18H16O3/c1-2-13(12-8-4-3-5-9-12)16-17(19)14-10-6-7-11-15(14)21-18(16)20/h3-11,13,19H,2H2,1H3
435-97-2Relevant articles and documents
An expedient solvent-free C-benzylation of 4-hydroxycoumarin with styrenes
Chatterjee, Rana,Mukherjee, Anindita,Santra, Sougata,Zyryanov, Grigory V.,Chupakhin, Oleg N.,Majee, Adinath
, p. 123 - 124 (2021/02/16)
An efficient straightforward solvent-free C(3)-benzylation of 4-hydroxycoumarin with styrenes is performed by heating the reactants in the presence of p-toluenesulfonic acid. By this procedure, benzylated 4-hydroxycoumarin derivatives which exhibit variou
Metal-Free C-O Bond Functionalization: Catalytic Intramolecular and Intermolecular Benzylation of Arenes
Bering, Luis,Jeyakumar, Kirujan,Antonchick, Andrey P.
supporting information, p. 3911 - 3914 (2018/07/22)
A catalytic, metal-free intramolecular rearrangement of benzyl phenyl ethers using nitrosonium salt as a catalyst is described. The optimized reaction conditions enabled a catalytic and metal-free Friedel-Crafts alkylation reaction with benzylic alcohols, producing water as the stoichiometric byproduct. A comprehensive scope (>50 examples) for both approaches and application in drug synthesis were demonstrated. Mechanistic studies suggest a Lewis acid-based mechanism for the metal-free Friedel-Crafts reaction.
Synthesis method of propafenone drug intermediate 3-(alpha-ethylbenzyl)-4-hydroxyl coumarin
-
Paragraph 0014; 0015; 0006, (2016/11/21)
A synthesis method of a propafenone drug intermediate 3-(alpha-ethylbenzyl)-4-hydroxyl coumarin includes the following steps that 0.21 mol of 4-hydroxyl coumarin and 0.26-0.29 mol of alpha-ethyl benzyl amine are added into a reaction vessel, the solution temperature is raised to 110-115 DEG C, the reaction time is 3-5 hours, the solution temperature is reduced to 10-15 DEG C, 300 ml of a potassium sulfite solution is added, acetonitrile is used for extracting the excessive alpha-ethyl benzyl amine, the solution is poured into 1.3 L of an oxalic acid solution, solid precipitation, filtration and washing with a saline solution are performed, a filter cake is added into 2.3 L of a potassium bromide solution, the solution temperature is raised to 90-95 DEG C and is kept for 2-3 hours, the solution temperature is reduced to 5-9 DEG C, solid precipitation, washing with cyclohexane and dehydration with a dehydrating agent are performed, and recrystallization is performed in nitromethane to obtain the crystal 3-(alpha-ethylbenzyl)-4-hydroxyl coumarin.
