5-Hydroxy-1H-imidazole-4-carboxamide Chemical Properties

Melting point:

260°C

Boiling point:

575.0±35.0 °C(Predicted)

Density 

1.627

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly), Water (Slightly)

form 

Solid

pka

7.20±0.15(Predicted)

color 

Grey

5-Hydroxy-1H-imidazole-4-carboxamide Usage And Synthesis

Chemical Properties

Grey Solid

Uses

5-Hydroxy-3H-imidazole-4-carboxamide (cas# 56973-26-3) is a compound useful in organic synthesis.

Definition

ChEBI: A hydroxyimidazole that is 5-hydroxyimidazole in which the hydrogen at position 4 is replaced by an aminocarbonyl group.

Synthesis

Under nitrogen protection, 20.0 g of 5-hydroxy-1H-imidazole-4-carboxamide hydrochloride dihydrate prepared according to the method of Reference Example 2 was dissolved in 240 mL of a 0.45 mol/L hydrochloric acid solution, and heated to 50°C to dissolve it completely. Maintaining the reaction temperature at 50 °C, 40 mL of an aqueous solution containing 14.3 g of sodium formate was added slowly and dropwise over 35 minutes. Upon completion of the reaction, the reaction mixture was cooled to an internal temperature of 5 °C and stirring was continued for 90 minutes. The resulting crystals were collected by filtration, and the crystals were washed sequentially using a mixture comprising 20 mL of acetone and 40 mL of water and 60 mL of acetone, resulting in 12.6 g of 5-hydroxy-1H-imidazole-4-carboxamide-3/4 hydrate, the product being a pale yellow crystal. The water content of the product was 8.6% (determined by Karl Fischer method). Infrared spectra (ATR method) showed characteristic absorption peaks located at 1655, 1619, 1584, 1551 cm?1. Powder X-ray diffraction pattern and infrared absorption spectra (ATR method) are demonstrated in Fig. 8, Table 3 and Fig. 9, respectively.

References

[1] Patent: EP2762469, 2014, A1. Location in patent: Paragraph 0144-0145
[2] Patent: US2015/51408, 2015, A1. Location in patent: Paragraph 0039

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