Sodium Acetate → Ethyl 4-amino-2-propyl-1H-imidazole-5-carboxylate

HRID 274602Notes

Reaction equation

HRID 274602 reaction equation
Cl.[C:2](=[NH:7])(OC)[CH2:3][CH3:4].[C:8](O)(=O)C(O)=O.[NH2:14][CH:15]([C:21]#[N:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17].C([O-])(=O)C.[Na+]>C(O)C>[NH2:22][C:21]1[N:7]=[C:2]([CH2:3][CH2:4][CH3:8])[NH:14][C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 6917117HCID 6917117, compoundHCID 12657463Methyl propanimidate--hydrogen chloride (1/1)

Product 1

HCID 20093493Ethyl 4-amino-2-propyl-1H-imidazole-5-carboxylateYield 74.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl propionimidate hydrochloride (4.8 g), ethyl 2-amino-2-cyanoacetate oxalate (4.0 g), anhydrous sodium acetate (9.1 g), and absolute ethanol (75 mL) was stirred at room temperature for 18 hours. Solids were removed by filtration and the filtrate was evaporated. The residue was partitioned between ethyl acetate and water. The ethyl acetate layer was washed with saturated NaCl, dried over MgSo4, and evaporated. Flash chromatography on silica gel, eluting with a gradient of dichloromethane-ethyl acetate (75:25) to ethyl acetate gives the title compound (2.7 g) as a pale yellow solid, mp 111°-114° C.; MS (DEI) 211 (m).

Workup

  1. customSolids were removed by filtration
  2. customthe filtrate was evaporated
  3. customThe residue was partitioned between ethyl acetate and water
  4. washThe ethyl acetate layer was washed with saturated NaCl
  5. customdried over MgSo4
  6. customevaporated
  7. washFlash chromatography on silica gel, eluting with a gradient of dichloromethane-ethyl acetate (75:25) to ethyl acetate

Sources & evidence

ORD record
ord-718d42002cfe4fa0a9c45efb7a10f5e6
Source dataset
uspto-grants-1995_02
Patent number
US05389661

Reaction notes

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