Ammonia → HCID 178488775, compound

HRID 2163552Notes

Reaction equation

HRID 2163552 reaction equation
O.O.O.C([O-])(=O)C.[Na+].N1C=CC=C(C=O)C=1.O.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([CH:28]=O)=O)=[CH:22][CH:21]=1.N.[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([C:37]2[NH:38]C=C[N:41]=2)[CH:32]=1>CO.O>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[N:41]=[C:37]([C:33]3[CH:32]=[N:31][CH:36]=[CH:35][CH:34]=3)[NH:38][CH:28]=2)=[CH:22][CH:21]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 103713-PyridinecarboxaldehydeHCID 123955003-(1H-Imidazol-2-yl)pyridineHCID 15556730(4-Methoxyphenyl)(oxo)acetaldehyde--water (1/1)HCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 178488775HCID 178488775, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium acetate trihydrate (5.8 g, 0.04 m), 3-pyridinecarboxaldehyde (2.3 g., 0.02 m), p-methoxyphenylglyoxal monohydrate (3.92 g., 0.02 m), water (20 ml.), concentrated aqueous ammonia (25 ml.), and methanol (75 ml.) is allowed to stand at room temperature overnight. The solution is concentrated to dryness under reduced pressure (20 mm) over steam, treated with saturated Na2CO3 (100 ml.) and extracted with chloroform (3 × 100 ml.). The organic layer is dried over Na2SO4, filtered and concentrated to dryness. The residue is chromatographed on silica gel (300 ml.) and the product eluted with 3-5% MeOH/CHCl3. The material is crystallized from acetonitrile to give 2.3 g. of 4-p-methoxyphenyl)-2-(3-pyridyl)imidazole of m.p. 184-186.

Workup

  1. concentrationThe solution is concentrated to dryness under reduced pressure (20 mm) over steam
  2. additiontreated with saturated Na2CO3 (100 ml.)
  3. extractionextracted with chloroform (3 × 100 ml.)
  4. dry with materialThe organic layer is dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe residue is chromatographed on silica gel (300 ml.)
  8. washthe product eluted with 3-5% MeOH/CHCl3
  9. customThe material is crystallized from acetonitrile
  10. customto give 2.3 g

Sources & evidence

ORD record
ord-28206df6ec19442b826490c85ea23990
Source dataset
uspto-grants-1979_01
Patent number
US04134983

Reaction notes

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