Sodium Hydroxide → HCID 178508045, compound

HRID 260409Notes

Reaction equation

HRID 260409 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([C:7]([O:9]CC)=[O:8])[NH:5][CH:6]=1.[OH-].[Na+]>C(O)C>[NH2:1][C:2]1[N:3]=[C:4]([C:7]([OH:9])=[O:8])[NH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178470299HCID 178470299, compound

Product 1

HCID 178508045HCID 178508045, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 4-amino-1H-imidazol-2-carboxylate (2.0 g, 12.9 mmol) (E. Gomez, C. Avendano and A. McKillop, Tetrahedron 1986, 42, 2635) in ethanol (50 ml) and 1M aqueous sodium hydroxide (14 ml) was refluxed for 20 minutes. The reaction mixture was concentrated to 20 ml and the pH of the solution adjusted to 5 with concentrated hydrogen chloride. The solid which precipitated, collected by filtration and washed with ethanol and ether to give the title compound (1.5 g, 32%). NMR: δ 7.07 (s, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated to 20 ml
  2. customThe solid which precipitated
  3. filtrationcollected by filtration
  4. washwashed with ethanol and ether

Sources & evidence

ORD record
ord-39251c6f1927469d8bcf2ba39b2002ad
Source dataset
uspto-grants-1996_06
Patent number
US05527793

Reaction notes

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