ETHYL 2-CHLOROOXAZOLE-4-CARBOXYLATE Chemical Properties

Melting point:

97-98℃

Boiling point:

254.1±32.0 °C(Predicted)

Density 

1.332±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

pka

-3.20±0.10(Predicted)

Appearance

White to pink Solid

InChI

InChI=1S/C6H6ClNO3/c1-2-10-5(9)4-3-11-6(7)8-4/h3H,2H2,1H3

InChIKey

SYWQOPRAPDMWMC-UHFFFAOYSA-N

SMILES

O1C=C(C(OCC)=O)N=C1Cl

CAS DataBase Reference

460081-18-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2934999090

ETHYL 2-CHLOROOXAZOLE-4-CARBOXYLATE Usage And Synthesis

Synthesis

Under nitrogen protection, 1.70 mL (14.3 mmol) of tert-butyl nitrite was added dropwise to a suspension of 1.65 g (12.3 mmol) cuprous(I) chloride in 50 mL of acetonitrile. The reaction mixture was heated to 75 °C, followed by the addition of 1.60 g (10.2 mmol) of ethyl 2-aminooxazole-4-carboxylate in batches over 20 min (Ref: G Crank MJ Foulis, J Med Chem 1971,14:1075-1077). Gases were released during the reaction. After continued stirring for 30 min, the reaction mixture was cooled to room temperature, diluted with 50 mL of ethyl acetate and washed with water (2 x 25 mL). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a dark oily solid. Purification by neutral silica gel column chromatography using a solvent mixture of hexane and ethyl acetate (3:1) afforded 1.27 g (71% yield) of the target compound, ethyl 2-chloroxazole-4-carboxylate, as white needle-like crystals (recrystallized from hexane). Mass spectrum (electrospray positive ion mode): m/z 176/177 [M+H]+. 1H NMR (CDCl3) δ: 1.47 (t, 3H, J = 7.16 Hz); 4.48 (q, 2H, J = 7.16 Hz); 8.28 (s, 1H).

References

[1] Organic Letters, 2003, vol. 5, # 16, p. 2911 - 2914
[2] Organic Letters, 2002, vol. 4, # 17, p. 2905 - 2907
[3] European Journal of Medicinal Chemistry, 2019, p. 80 - 108
[4] Patent: WO2005/26149, 2005, A1. Location in patent: Page/Page column 111
[5] Journal of Medicinal Chemistry, 2010, vol. 53, # 9, p. 3814 - 3830

ETHYL 2-CHLOROOXAZOLE-4-CARBOXYLATE(460081-18-9)Related Product Information

• 4-Oxazolecarboxylic acid, 2-amino-, ethyl ester
• ETHYL 2-AMINOOXAZOLE-4-CARBOXYLATE
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• (2-CHLOROOXAZOL-4-YL)METHANOL
• 2-Chlorooxazole-4-carboxylic acid
• 2-Chloroxazole
• ETHYL 2-CHLOROOXAZOLE-4-CARBOXYLATE