ETHYL 4-AMINO-2-(METHYLTHIO)-1,3-THIAZOLE-5-CARBOXYLATE

ETHYL 4-AMINO-2-(METHYLTHIO)-1,3-THIAZOLE-5-CARBOXYLATE Property

Melting point:

100-102 °C(Solv: ethanol (64-17-5))

Boiling point:

368.6±45.0 °C(Predicted)

Density 

1.37±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

1.09±0.10(Predicted)

Appearance

Light yellow to light brown Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

ETHYL 4-AMINO-2-(METHYLTHIO)-1,3-THIAZOLE-5-CARBOXYLATE Chemical Properties,Usage,Production

Synthesis Reference(s)

Tetrahedron Letters, 7, p. 1885, 1966 DOI: 10.1016/0005-2760(66)90119-6

Synthesis

Synthesis of ethyl 4-amino-2-(methylthio)thiazole-5-carboxylate: ethyl 2-mercaptoacetate (50 g, 0.416 mol) was dissolved in 500 ml of dimethylformamide (DMF), followed by the addition of N-cyanoimino-S,S-dimethyl-dithiocarbonate (67 g, 0.416 mol) and diisopropylamine (112 ml, 0.624 mol). The reaction mixture was heated and stirred at 100 °C for 5 hours. After completion of the reaction, the mixture was poured into 500 ml of saturated ammonium chloride solution and extracted with 500 ml of ethyl acetate. The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting solid was washed with hexane to give ethyl 2-methylthio-4-aminothiazole-5-carboxylate (90 g, 99% yield). The product was characterized by 1H-NMR (400 MHz, CDCl3): δ 5.84 (broad single peak, 2H), 4.26 (quadruple peak, J=7.2 Hz, 2H), 2.63 (single peak, 3H), 1.32 (triple peak, J=7.2 Hz, 3H); LC-MS showed the molecular ion peak m/z 219 (MH+).

References

[1] Patent: US2013/72482, 2013, A1. Location in patent: Paragraph 0315-0317
[2] Patent: WO2015/89327, 2015, A1. Location in patent: Paragraph 0468
[3] Tetrahedron Letters, 1966, # 17, p. 1885 - 1889
[4] Patent: WO2015/193506, 2015, A1. Location in patent: Page/Page column 57-58