2-(2-Aminothiazole-4-yl)-2-methoxyiminoacetic acid Chemical Properties

Melting point:

192 °C (dec.)(lit.)

Boiling point:

425.1±37.0 °C(Predicted)

Density 

1.463 (estimate)

refractive index 

1.6630 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO (Slightly), Methanol (Slightly, Heated)

pka

2.97±0.10(Predicted)

form 

solid

color 

White to Off-White

Water Solubility 

0.6 g/100 mL (20 ºC)

λmax

273nm(MeOH)(lit.)

InChI

InChI=1S/C6H7N3O3S/c1-12-9-4(5(10)11)3-2-13-6(7)8-3/h2H,1H3,(H2,7,8)(H,10,11)/b9-4+

InChIKey

NLARCUDOUOQRPB-RUDMXATFSA-N

SMILES

C1(=CSC(N)=N1)/C(/C(=O)O)=N\OC

CAS DataBase Reference

65872-41-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-24/25

WGK Germany 

3

HS Code 

29349990

MSDS

• Language:English Provider:2-Amino-alpha-(methoxyimino)-4-thiazoleacetic acid
• Language:English Provider:ACROS

2-(2-Aminothiazole-4-yl)-2-methoxyiminoacetic acid Usage And Synthesis

Chemical Properties

OFF-WHITE TO BEIGE POWDER

Uses

Intermediate in the preparation of Cephem compounds.

Synthesis

General procedure for the synthesis of aminothiazole acid from ethyl (Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate (Example 2): in a 250 ml reaction vial, 45.9 g (0.2 mol) of ethyl (Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetate was suspended in 200 ml of ethanol, followed by the addition of 1 N sodium hydroxide aqueous solution. The reaction mixture was stirred at room temperature for 15 hours. Upon completion of the reaction, the pH of the reaction solution was adjusted to 7.0 with 10% aqueous hydrochloric acid, followed by distillation under reduced pressure to remove the ethanol. The aqueous phase was washed with ethyl acetate and the pH was adjusted again with 10% aqueous hydrochloric acid to 2.8. Stirring was carried out under cooling conditions in an ice bath to induce the precipitation of crystals. The crystals were separated by filtration, washed with acetone and finally recrystallized from ethanol to give 22.9 g of 2-(2-aminothiazol-4-yl)-2-(Z)-methoxyiminoacetic acid in 57.0% yield.

References

[1] Patent: EP859002, 1998, A1

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