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ChemicalBook CAS DataBase List 4-Amino-5-imidazolecarboxamide hydrochloride

4-Amino-5-imidazolecarboxamide hydrochloride synthesis

1synthesis methods
4-Amino-5-imidazolecarboxamide hydrochloride is white or off-white crystalline, mainly used as a pharmaceutical intermediate for the synthesis of dacarbamine and akamin. It can be synthesised by using α-amidinoacetamide hydrochloride, aniline and formic acid as raw materials through diazotization, coupling, reduction, formylation and cyclization.
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Yield:-

Reaction Conditions:

with hydrogenchloride;sodium nitrite in water

Steps:

1 Preparation of 5-diazo-5H-imidazole-4 carboxamide
Example 1 Preparation of 5-diazo-5H-imidazole-4 carboxamide 47 g of sodium nitrite was dissolved in 1.2 litres of water and the solution cooled to 0° C. 100 g of 5-aminoimidazole-4 carboxamide was dissolved in a solution of hydrochloric acid (80 ml of 36% HCL in 720 ml water) with stirring, and the resultant 5-aminoimidazole-4 carboxamide hydrochloride solution was added slowly, drop-wise over a period of 20-30 minutes at 0-5° C. After the addition was completed, the reaction mixture was stirred for 10 minutes and filtered. The solid obtained was suspended in 400 ml DM water and stirred for 15 minutes. The suspension was filtered and suction dried for 15 mins. The obtained solid was suspended in 500 ml of THF and stirred for 15 minutes. The suspension was filtered and suction dried for 15 minutes. Finally, the solid was dried at 45° C. to afford 60 gms of the title compound. Purity: 96.4% by HPLC.

References:

Gupte, Rajan;Rohit, Chaturvedi;Pravin, Baviskar US2011/230658, 2011, A1

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