Imidazole → HCID 18921818, compound

HRID 327155Notes

Reaction equation

HRID 327155 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[OH-:6].[Na+].Cl[C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[OH:16]>CN(C=O)C>[Cl:15][C:13]1[CH:12]=[CH:11][C:10]([OH:16])=[CH:9][C:14]=1[O:6][CH2:13][CH2:14][CH2:9][CH2:10][CH2:11][CH2:12][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 84492,4-DichlorophenolHCID 14798Sodium Hydroxide

Product 1

HCID 18921818HCID 18921818, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add imidazole (25 g) and NaOH (15 g) to DMF (250 ml) and stir for I hour. Add the product of part (a) (8.65 g) and stir overnight. Evaporate the solvent, partition the resultant residue with water/dichloromethane (adjust aqueous layer to pH 7 with potassium phosphate), separate organic layer and evaporate solvent. Purify the resultant residue on a silica column to obtain the title compound, MS: m/z 295 (M+ +1).

Workup

  1. stirringstir overnight
  2. customEvaporate the solvent
  3. custompartition the resultant residue with water/dichloromethane (adjust aqueous layer to pH 7 with potassium phosphate)
  4. customseparate organic layer
  5. customevaporate solvent
  6. customPurify the resultant residue on a silica column

Sources & evidence

ORD record
ord-1b70fd0c797045208b0336103fefa309
Source dataset
uspto-grants-1993_12
Patent number
US05272167

Reaction notes

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