2-Amino-2-cyanoacetamide → HCID 178468825, compound

HRID 1809968Notes

Reaction equation

HRID 1809968 reaction equation
C(S[C:9]([CH2:11][C:12]1[O:16][C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:14][CH:13]=1)=[NH:10])C1C=CC=CC=1.[NH2:22][CH:23]([C:27]#[N:28])[C:24]([NH2:26])=[O:25].C(=O)([O-])O.[Na+]>CO>[NH2:28][C:27]1[NH:10][C:9]([CH2:11][C:12]2[O:16][C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:14][CH:13]=2)=[N:22][C:23]=1[C:24](=[O:25])[NH2:26]

Participants

5

Reactant 3

HCID 983412-Amino-2-cyanoacetamideHCID 516892Sodium BicarbonateHCID 68869433HCID 68869433, compound

Product 1

HCID 178468825HCID 178468825, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

30.5 g (0.09 M) of ethyl 5-benzylsulfanylcarbonimidoylmethylfuran-2-carboxylate, 8.9 g (0.09 M) of aminocyanoacetamide and 7.5 g (0.09 M) of sodium hydrogen carbonate in 180 ml of methanol are refluxed with stirring for 5 hours. The crude product obtained is purified by chromatography on silica using a dichloromethane/methanol mixture (90/10) as eluent, to give 17 g of ethyl 5-(5-amino-4-carbamoyl-1H-imidazol-2-ylmethyl)furan-2-carboxylate in the form of a vitreous brown solid.

Workup

  1. customThe crude product obtained
  2. customis purified by chromatography on silica using a dichloromethane/methanol mixture (90/10) as eluent

Sources & evidence

ORD record
ord-294756c7177f44b19ee1e4875e6c9efc
Source dataset
uspto-grants-2013_01
Patent number
US08362057B2

Reaction notes

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