53648-05-8 Usage
Originator
Ibudros,Manetti-Roberts,Italy,1978
Uses
rac Ibuproxam is a poorly water-soluble anti-inflammatory drug.
Definition
ChEBI: A hydroxamic acid obtained by formal condensation of the carboxy group of ibuprofen with the amino group of hydroxylamine. Used for treatment of pain and inflammation associated with musculoskeletal and joint disorders.
Manufacturing Process
In a 1,000 ml three-necked flask equipped with a stirrer, a dropping funnel
and a silica gel guard pipe, 46.7 g hydroxylamine hydrochloride are dissolved
cold in 480 ml methanol. Separately a solution of 56.1 g KOH in 280 ml
methanol is prepared, heated to 30°C and admixed, dropwise under stirring to
the hydroxylamine solution. All successive temperature increases during this
admixture are prevented by cooling in an ice bath. After the whole KOH
solution has been admixed, the mixture is left standing for 5 minutes so as to
attain the complete precipitation of the KCl.Separately, 72.02 g ethyl 2-(4-isobutylphenyl)-propionate, obtained by the
esterification of 2-(4-isobutylphenyl)-propionic acid with ethanol and
concentrated H2SO4, are solved with 100 ml methanol, this solution is
introduced drop by drop into the reaction flask, and stirred and cooled for 5 hours on an ice bath. Thereafter it is suction filtered, the residue is washed
with all together 50 ml methanol, the wash is added to the filtrate, thereafter
the whole is evaporated in a water bath with a rotating evaporator at a
reduced pressure, until 100-200 ml of a concentrated solution are obtained.
This solution is poured into a 200 ml beaker into which are stirred
approximately 1,000 ml 1.25N acetic acid. This mixture is left standing for 24
hours, thereafter suction filtered. The resulting filtrate is taken up with 100 ml
petroleum ether at 40°C to 60°C, in order to solve any possible residue of
unreacted starting ester, and refiltered. Approximately 50g of 2-(4-
isobutylphenyl)-propiohydroxamic acid are obtained, having a melting point of
119°C to 121°C on Kofler's hot stage.
Therapeutic Function
Antiinflammatory
Check Digit Verification of cas no
The CAS Registry Mumber 53648-05-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,3,6,4 and 8 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 53648-05:
(7*5)+(6*3)+(5*6)+(4*4)+(3*8)+(2*0)+(1*5)=128
128 % 10 = 8
So 53648-05-8 is a valid CAS Registry Number.
InChI:InChI=1/C13H19NO2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(15)14-16/h4-7,9-10,16H,8H2,1-3H3,(H,14,15)
53648-05-8Relevant articles and documents
P(III)-Assisted Electrochemical Access to Ureas via in situ Generation of Isocyanates from Hydroxamic Acids
Meng, Haiwen,Sun, Kunhui,Xu, Zhimin,Tian, Lifang,Wang, Yahui
supporting information, p. 1768 - 1772 (2021/03/26)
An external oxidant-free protocol for the generation of isocyanates from hydroxamic acids assisted by trivalent phosphine under mild electrochemical conditions was reported. The process started with the anodic oxidation of hydroxamic acids, followed by reacting with phosphine to form corresponding alkoxyphosphoniums and subsequent rearrangement with the release of tri-substituted phosphine oxide as the driving force to give isocyanates, which were trapped by N-based nucleophiles to produce various ureas. This method provides a broadly applicable procedure to access isocyanate intermediates under mild electrochemical conditions.
Intermolecular, Branch-Selective, and Redox-Neutral Cp*IrIII-Catalyzed Allylic C?H Amidation
Knecht, Tobias,Mondal, Shobhan,Ye, Jian-Heng,Das, Mowpriya,Glorius, Frank
supporting information, p. 7117 - 7121 (2019/04/30)
Herein, we report the redox-neutral, intermolecular, and highly branch-selective amidation of allylic C?H bonds enabled by Cp*IrIII catalysis. A variety of readily available carboxylic acids were converted into the corresponding dioxazolones and efficiently coupled with terminal and internal olefins in high yields and selectivities. Mechanistic investigations support the formation of a nucleophilic IrIII–allyl intermediate rather than the direct insertion of an Ir–nitrenoid species into the allylic C?H bond.
