Sodium Hydroxide → HCID 178484896, compound

HRID 358257Notes

Reaction equation

HRID 358257 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][NH:11][CH:12]=2)=[CH:4][CH:3]=1.Cl.[CH3:14][N:15]=[CH:16]OCC.[OH-].[Na+]>C(O)C>[CH3:14][NH:15][CH:16]=[N:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[CH:10][NH:11][CH:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 12210271ethyl N-methyl-formimidate hydrochlorideHCID 178507418HCID 178507418, compound

Product 1

HCID 178484896HCID 178484896, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 0.8 gm of 4-(4-aminophenyl)-1-H-imidazole and 1.86 gm of ethyl N-methyl-formimidate hydrochloride [F. H. Suydam et al., J. Org. Chem. 34, 292 (1969)] in 20 ml of anhydrous ethanol was stirred at room temperature for two days. The clear solution was evaporated to dryness, and the oily residue was dissolved in water. The solution so obtained was adjusted to pH 10 with 10% NaOH. The product which separated was extracted with ethyl acetate, the organic solution was evaporated to dryness, and the product obtained was purified through its hydorchloride salt to give 0.35 gm of the desired compound as crystalline solid.

Workup

  1. customThe clear solution was evaporated to dryness
  2. dissolutionthe oily residue was dissolved in water
  3. customThe solution so obtained
  4. customThe product which separated
  5. extractionwas extracted with ethyl acetate
  6. customthe organic solution was evaporated to dryness
  7. customthe product obtained
  8. customwas purified through its hydorchloride salt

Sources & evidence

ORD record
ord-d3b976f6f6d8451c91d2eac5a94e0ee4
Source dataset
uspto-grants-1984_08
Patent number
US04465841

Reaction notes

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