N-(Tetrahydro-2-oxo-3-thienyl)-acetamide Property

Melting point:

109-111 °C

Boiling point:

427.3±34.0 °C(Predicted)

Density 

1.202 (estimate)

refractive index 

1.5500 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO : ≥ 50 mg/mL (314.05 mM)

pka

14.62±0.20(Predicted)

form 

solid

color 

White to Almost white

Merck 

14,2320

EPA Substance Registry System

Citiolone (1195-16-0)

Safety

Hazard Codes 

T,Xi

Risk Statements 

25-36/37/38

Safety Statements 

22-24/25-45-36-26

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

AC8680000

TSCA 

Yes

HS Code 

2934.99.9001

Toxicity

LD50 i.v. in mice: 1200 mg/kg (Kirnberger)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

Precautionary statements

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

N-(Tetrahydro-2-oxo-3-thienyl)-acetamide Chemical Properties,Usage,Production

Chemical Properties

Acicular crystals.maximum UV absorption 238 nm.

Originator

Citiolase,Roussel Maestretti France,1970

Uses

hepatoprotectant, free radical scavenger

Uses

Photographic antifogging agent: Dersch, US 3068100 (1962); Weber, DE 1164828 (1964 to Adox Fotowerke Schleussner GmbH), C.A. 60, 14050f (1964); protector against radiation: Langendorff, Koch, Strahlentherapie 106, 451 (1958); Braun et al., ibid. 108, 262 (1959), C.A. 52, 18841h (1958); 53, 17325e (1959).

Definition

ChEBI: N-(2-oxo-3-thiolanyl)acetamide is a N-acyl-amino acid.

Manufacturing Process

12.73 kg of acetyl methionine are gradually introduced into a brine-cooled
pressure-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.]