1195-16-0 Usage
Description
N-(Tetrahydro-2-oxo-3-thienyl)-acetamide is an organic compound with a unique chemical structure that features a tetrahydrothiophene ring and an amide functional group. It is characterized by its acicular crystal form and exhibits maximum UV absorption at 238 nm.
Uses
Used in Pharmaceutical Industry:
N-(Tetrahydro-2-oxo-3-thienyl)-acetamide is used as a hepatoprotectant, which helps protect and support liver function. It is also utilized as a free radical scavenger, playing a crucial role in neutralizing harmful free radicals and preventing oxidative stress-related damage.
Used in Photographic Industry:
N-(Tetrahydro-2-oxo-3-thienyl)-acetamide serves as a photographic antifogging agent, as documented in patents by Dersch (US 3068100, 1962) and Weber (DE 1164828, 1964 to Adox Fotowerke Schleussner GmbH). Its application helps improve the quality and clarity of photographic images by preventing fogging.
Used in Radiation Protection:
N-(Tetrahydro-2-oxo-3-thienyl)-acetamide acts as a protector against radiation, as demonstrated in studies by Langendorff and Koch (Strahlentherapie 106, 451, 1958) and Braun et al. (ibid 108, 262, 1959). This property makes it valuable in various applications where radiation protection is necessary, such as in medical and industrial settings.
Originator
Citiolase,Roussel Maestretti France,1970
Manufacturing Process
12.73 kg of acetyl methionine are gradually introduced into a brine-cooledpressure-tight apparatus provided with a stirrer and containing 140 liters of
liquid ammonia at -50°C. The amino acid is dissolved after a short time; 6.5
kg of sodium metal are then introduced over a period of from 4 to 5 hours at
a temperature of from -40°C to 60°C. Eventually, a persistent blue coloration
of the ammoniacal solution indicates the end of the reaction. The ammonia is
distilled off and the residue is taken up in 70 liters of methanol. In order to
remove ammonia which has been formed from sodium amide, 30 to 40 liters
of methanol are distilled off and the residue is made up with methanol to 80
liters. The strongly alkaline solution is neutralized with 22 liters of
concentrated aqueous hydrochloric acid. The solution is filtered off from the
precipitated sodium chloride and evaporated to dryness in vacuo. The closing
of the thiolactone ring takes place as a result of the evaporation of the
solution to dryness in the acid pH range and the N-acetyl homocystein
originally present is converted into N-acetyl homocystein thiolactone. In order
to isolate this compound, the residue is recrystallized from 25% aqueous
alcohol.
9 kg of N-acetyl homocystein thiolactone are obtained, this corresponding to a
yield of 85% of the theoretical.
Therapeutic Function
Hepatoprotectant
Purification Methods
Dry Citiolone in a vacuum desiccator. It recrystallises from toluene as needles. It is a ninhydrin -ve substance which gives a “slow” nitroprusside test. It has max at 238nm ( 4,400 M-1cm-1); and (nujol) 1789s and 851ms cm. [Benesch & Benesch J Am Chem Soc 78 1597max 1956, cf Laliberté J Chem Soc 2756 1963.]
Check Digit Verification of cas no
The CAS Registry Mumber 1195-16-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,1,9 and 5 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 1195-16:
(6*1)+(5*1)+(4*9)+(3*5)+(2*1)+(1*6)=70
70 % 10 = 0
So 1195-16-0 is a valid CAS Registry Number.
InChI:InChI=1/C6H9NO2S/c1-4(8)7-5-2-3-10-6(5)9/h5H,2-3H2,1H3,(H,7,8)/t5-/m0/s1
1195-16-0Relevant articles and documents
Synthesis of sequence-ordered polymers via sequential addition of monomers in one pot
Yan, Jun-Jie,Wang, Di,Wu, De-Cheng,You, Ye-Zi
, p. 6057 - 6059 (2013)
Sequence-ordered polymers can be simply prepared in one pot via sequential monomer addition.
Preparation Method for Homocystein Thiolactone or Selenolactone
-
Paragraph 0037-0040, (2021/09/14)
The present invention provides an expensive reagent such as homocysteine thiolactone or selenolactone as the main intermediate of erdosteine, or an expensive reagent such as HI. More specifically, A) a homoserine lactone or N - protected homoserine is reacted with a thiocarboxylic acid metal salt or selenocarboxylic acid metal salt (RCOXM, X=S or Se). B) Step A) of producing homocysteine thiolactone or homocysteine sonoactone by deprotection of N - protected homocysteine thiolactone or N - protected homocysteine seleactone. The present invention relates to a method for producing homocysteine thiactone or homocysteine senolactone or a salt thereof by the following reaction scheme. [Reaction Scheme] Then, this time. X Is S or Se, R and R ' are independently alkyl or aryl which is C1 - C6, and M is Na or K.
Two tandem multicomponent reactions for the synthesis of sequence-defined polymers
Yang, Lu,Zhang, Ze,Cheng, Bofei,You, Yezi,Wu, Decheng,Hong, Chunyan
, p. 1734 - 1740 (2015/11/02)
Multicomponent polymerizations have become powerful tools for the construction of sequence-defined polymers. Although the Passerini multicomponent reaction has been widely used in the synthesis of sequence-defined polymers, the tandem usage of the Passerini multicomponent reaction and other multicomponent reactions in one-pot for the synthesis of sequence-defined polymers has not been developed until now. In this contribution, we report the tandem usage of the Passerini three-component reaction and the three-component amine-thiol-ene conjugation reaction in one pot for the synthesis of sequence-defined polymers. The Passerini reaction between methacrylic acid, adipaldehyde, and 2-isocyanobutanoate was carried out, affording a new molecule containing two alkene units. Subsequently, an amine and a thiolactone were added to the reaction system, whereupon the three-component amine-thiol-ene conjugating reaction occurred to yield a sequence-defined polymer. This method offers more rapid access to sequence-defined polymers with high molecular diversity and complexity.