2-Aminothiazole

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2-Aminothiazole
2-Aminothiazole.svg
2-Aminothiazole-3D-spacefill.png
Names
Preferred IUPAC name
1,3-Thiazol-2-amine
Other names
2-Thiazolamine, Aminothiazole, 2-Thiazylamine, Basedol, 2-Thiazolylamine, 4-Thiazolin-2-onimine, 2-Amino-1,3-thiazole, Abadole
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.284 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-511-6
KEGG
PubChem CID
UNII
  • InChI=1S/C3H4N2S/c4-3-5-1-2-6-3/h1-2H,(H2,4,5) Yes check.svgY
    Key: RAIPHJJURHTUIC-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C3H4N2S/c4-3-5-1-2-6-3/h1-2H,(H2,4,5)
    Key: RAIPHJJURHTUIC-UHFFFAOYAZ
  • c1csc(n1)N
Properties
C3H4N2S
Molar mass 100.14 g·mol−1
AppearanceLight yellow crystals
Melting point 86 to 89 °C (187 to 192 °F; 359 to 362 K)
Boiling point 117 °C (243 °F; 390 K) (20 hPa)
100 g/L (20 °C)
−56.0·10−6 cm3/mol
Hazards
GHS labelling: [1]
GHS-pictogram-exclam.svg
Warning
H302, H319
P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P330, P337+P317, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
0
0
600 °C (1,112 °F; 873 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

2-Aminothiazole is a heterocyclic amine featuring a thiazole core. It can also be considered a cyclic isothiourea. It possesses an odor similar to pyridine and is soluble in water, alcohols and diethyl ether. 2-Aminothiazole itself is mainly of academic interest, with few exceptions. It is a precursor to a sulfathiazole ("sulfa drugs"). 2-Aminothiazole can be used as a thyroid inhibitor in the treatment of hyperthyroidism. [2]

Contents

2-Aminothiazole is prepared from paraldehyde, thiourea, and sulfuryl chloride. [3]

2-Aminothiazoles

Like the parent, 2-aminothiazoles are often produced by the condensation of thiourea and an alpha-halo ketone. [4] [5] [6]

Hantsch Thiazole Synthesis HantzschThiazole-Synthesis.png
Hantsch Thiazole Synthesis

In an adaptation of the Robinson-Gabriel synthesis, a 2-acylamino-ketone reacts with phosphorus pentasulfide.

Applications

Synthetic aminothiazoles - compounds containing the parent 2-aminothiazole as a subunit - are used in medicinal chemistry. Some examples are abafungin, acotiamide, amiphenazole, amthamine, avatrombopag, aztreonam, cefepime, cefixime, ceftizoxime, ceftiofur, ceftibuten, cefpirome, famotidine, meloxicam, and pramipexole. [7] [8]

References

  1. ↑ "2-Aminothiazole". pubchem.ncbi.nlm.nih.gov. Retrieved 12 December 2022.
  2. ↑ Dahlmanns, Simone M.; Müller-Gärtner, Hans-Wilhelm (2000). "Thyrotherapeutic Agents". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a27_039. ISBN   9783527303854.
  3. ↑ Erlenmeyer, H.; Herzfeld, L.; Prijs, B. (1955). "Zur Synthese von 2-Amino-thiazolderivaten". Helvetica Chimica Acta. 38 (5): 1291–1294. doi:10.1002/hlca.19550380529.
  4. ↑ J. R. Byers; J. B. Dickey (1939). "2-Amino-4-methylthiazole". Organic Syntheses . 19: 10. doi:10.15227/orgsyn.019.0010 .
  5. ↑ Gómez, Antonio Bermejo; Ahlsten, Nanna; Platero-Prats, Ana E.; Martín-Matutejournal=Organic Syntheses, Belén (2014). "Synthesis of 4,5-Disubstituted 2-Aminothiazoles from α,β-Unsaturated Ketones: Preparation of 5-Benzyl-4-methyl-2-aminothiazolium Hydrochloride Salt". Organic Syntheses. 91: 185–200. doi: 10.15227/orgsyn.091.0185 .
  6. ↑ Alajarín, M.; Cabrera, J.; Pastor, A.; Sánchez-Andrada, P.; Bautista, D. (2006). "On the [2+2] Cycloaddition of 2-Aminothiazoles and Dimethyl Acetylenedicarboxylate. Experimental and Computational Evidence of a Thermal Disrotatory Ring Opening of Fused Cyclobutenes". J. Org. Chem. 71 (14): 5328–5339. doi:10.1021/jo060664c. PMID   16808523.
  7. ↑ Das, Debasis; Sikdar, Papiya; Bairagi, Moumita (2016). "Recent Developments of 2-Aminothiazoles in Medicinal Chemistry". European Journal of Medicinal Chemistry. 109: 89–98. doi:10.1016/j.ejmech.2015.12.022. PMID   26771245.
  8. ↑ Wan, Yichao; Long, Jiabing; Gao, Han; Tang, Zilong (2021). "2-Aminothiazole: A privileged scaffold for the discovery of anti-cancer agents". European Journal of Medicinal Chemistry. 210. doi:10.1016/j.ejmech.2020.112953. PMID   33148490. S2CID   226258989.
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