Imidazole → HCID 23316957, compound

HRID 1982535Notes

Reaction equation

HRID 1982535 reaction equation
[NH:1]([C:5]1[CH:6]=[C:7]([C:12](=O)[CH2:13][CH2:14][CH2:15]Br)[CH:8]=[CH:9][C:10]=1[Cl:11])C(C)=O.[NH:18]1[CH:22]=[CH:21][N:20]=[CH:19]1>>[NH2:1][C:5]1[CH:6]=[C:7]([C:12]2[C:19]3[N:18]([CH:22]=[CH:21][N:20]=3)[CH2:15][CH2:14][CH:13]=2)[CH:8]=[CH:9][C:10]=1[Cl:11]

Participants

3

Reactant 2

HCID 795ImidazoleHCID 13633266HCID 13633266, compound

Product 1

HCID 23316957HCID 23316957, compound

Procedure

Combine 5 g (15.7 mmol) of 3'-acetamino-4-bromo-4'-chlorobutyrophenone with 15 g (0.22 mol) of imidazole, and heat to 175° C. for 18 hr. Isolate the crude product by crystallization from ether, and add to a solution of 5 g of potassium hydroxide in 20 ml of 1:1 solution of methanol/water. Heat to reflux for 2 hr. Cool to room temperature, and pour the reaction mixture into 100 ml of water with rapid stirring. The resulting precipitate is recrystallized from ether to provide the title compound.

Workup

  1. customIsolate the crude product
  2. customby crystallization from ether
  3. additionadd to a solution of 5 g of potassium hydroxide in 20 ml of 1:1 solution of methanol/water
  4. temperatureHeat
  5. temperatureto reflux for 2 hr
  6. additionpour the reaction mixture into 100 ml of water with rapid stirring
  7. customThe resulting precipitate is recrystallized from ether

Sources & evidence

ORD record
ord-3d219a3ca17642dfa1b1c51245220b37
Source dataset
uspto-grants-1986_06
Patent number
US04596872

Reaction notes

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