HCID 12318256, compound → ethyl 4-amino-1-methyl-1H-imidazole-5-carboxylate

HRID 1728340Notes

Reaction equation

HRID 1728340 reaction equation
[NH2:1][C:2]1[N:3]=[C:4](SC)[N:5]([CH3:12])[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]>[Ni].C(O)C>[NH2:1][C:2]1[N:3]=[CH:4][N:5]([CH3:12])[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 1

HCID 12318256HCID 12318256, compound

Product 1

HCID 12298751ethyl 4-amino-1-methyl-1H-imidazole-5-carboxylateYield 60%

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst3×HCID 702EthanolSolvent

Procedure

Ethyl 4-amino-1-methyl-2-(methylthio)imidazole-5-carboxylate (1.52 g, 7.11 mmol) and W-2 Raney nickel (3 g, 50% in water) in ethanol (25 mL) were heated at reflux for 12 hours. Additional Raney nickel (ca 1.5 g, 50% in water) was added and heating was continued for an additional 3 hours adding Raney nickel (ca 1.5 g, 50% in water) every hour. The reaction was filtered and the filtrate evaporated under reduced pressure. Chromatography of the residue on silica gel eluting with 1.5% methanol in chloroform afforded 0.72 g (60%) of the desired product as a solid. TLC (10% methanol/90% chloroform) Rf =0.47. 1H NMR (CDCl3, 300 MHz) d 1.38 (t, 3H), 3.77 (s, 3H), 4.32 (q, 2H), 4.82 (br, 2H), 7.13 (s, 1H). MS (DCl/NH3) m/e 170 (M+H)+ .

Workup

  1. temperatureat reflux for 12 hours
  2. temperatureheating
  3. filtrationThe reaction was filtered
  4. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-51fea89c81af4ada8f7a3e2683b007c6
Source dataset
uspto-grants-1994_07
Patent number
US05326776

Reaction notes

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