Hydrochloric Acid → 5-Aminoimidazole-4-carboxamide

HRID 1008253Notes

Reaction equation

HRID 1008253 reaction equation
[OH-:1].[Na+].[NH2:3][C:4](C#N)=[C:5]([NH:8][CH:9]=[NH:10])[C:6]#[N:7].Cl>O>[CH:9]1[NH:8][C:5]([C:4]([NH2:3])=[O:1])=[C:6]([NH2:7])[N:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178511348HCID 178511348, compound

Product 1

HCID 96795-Aminoimidazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Water (50 ml) and an aqueous solution of 25% NaOH (43.0 g) were added to 8 g of N-(2-amino-1,2-dicyanovinyl) formamidine (hereinafter abbreviated as AMD), and reacted under reflux for 2 hours. This aqueous solution was cooled to room temperature or below and adjusted the pH to 7 by adding 35% hydrochloric acid. The reaction solution was concentrated and exsiccated under reduced pressure followed by adding ethanol, and subsequently insoluble sodium chloride was filtrated and removed. The filtrate was treated with activated carbon and then concentrated to afford an ethanol solution of AICA. To lower the pH to 3 or less, 35% hydrochloric acid was added to this, cooled to 10° C. or less, and subsequently generated crystal was filtrated. This crystal was dried to yield 8.1 g of 4(5)-aminoimidazole-5-carboxamide (hereinafter abbreviated as AICA) hydrochloride (yield: 84%).

Workup

  1. customreacted
  2. temperatureunder reflux for 2 hours
  3. temperatureThis aqueous solution was cooled to room temperature or below
  4. concentrationThe reaction solution was concentrated
  5. additionby adding ethanol, and subsequently insoluble sodium chloride
  6. filtrationwas filtrated
  7. customremoved
  8. additionThe filtrate was treated with activated carbon
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-c41b8b4311874c81ad9f8b5f69e07842
Source dataset
uspto-grants-2004_09
Patent number
US06797828B1

Reaction notes

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