Imidazole → HCID 68463439, compound

HRID 505679Notes

Reaction equation

HRID 505679 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C(N([CH2:11][CH3:12])CC)C.C1(C)C=CC([C:19](Cl)=[O:20])=CC=1.[OH-:23].[Na+].N1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:19]([O:20][C:28]1[CH:29]=[CH:30][C:11]([CH3:12])=[CH:26][CH:27]=1)=[O:23]

Participants

7

Reactant 5

HCID 795ImidazoleHCID 1049Pyridine2×HCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 14798Sodium Hydroxide

Product 1

HCID 68463439HCID 68463439, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To imidazole (6.80 g, 100 mmol) in pyridine (30 ml) was added triethylamine (20.2 g, 200 mmol) and the mixture was stirred under ice cooling. Therein was dropped p-toluoyl chloride (30.9 g, 200 mmol) in a period of 10 minutes. After addition of pyridine (70 ml) the mixture was stirred for 3 hours at room temperature. Thereto was added 4N aqueous sodium hydroxide solution (100 ml) and the mixture was stirred 3 hours at 80° C. The reaction mixture was allowed to stand at room temperature. After addition of water (200 ml), the mixture was stirred to give crystals. The crystals were taken by filtration and washed with water-methanol (1:1) to give the subject compound (9.83 g, 51%).

Workup

  1. stirringwas stirred for 3 hours at room temperature
  2. stirringthe mixture was stirred 3 hours at 80° C
  3. customto stand at room temperature
  4. stirringthe mixture was stirred
  5. customto give crystals
  6. filtrationThe crystals were taken by filtration
  7. washwashed with water-methanol (1:1)

Sources & evidence

ORD record
ord-0e3071cc77114e08a1f569ca776a52b4
Source dataset
uspto-grants-2010_08
Patent number
US07781479B2

Reaction notes

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