Imidazole → 2,4-Dichloro-beta-(1-imidazolyl)propiophenone

HRID 442508Notes

Reaction equation

HRID 442508 reaction equation
C(C(C1C=[CH:9][C:8]([Cl:11])=[CH:7]C=1Cl)=O)=C.[Cl:13][C:14]1[CH:19]=C(Cl)C=CC=1C(C=C)O.Br[C:26]1[C:27](=O)[C:28](Br)=[CH:29][C:30](Br)(Br)[CH:31]=1.[NH:36]1C=C[N:38]=[CH:37]1.CC[O:43]CC>>[Cl:11][CH:8]([CH2:7][N:36]1[CH:19]=[C:14]([Cl:13])[N:38]=[CH:37]1)[C:9]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:43]

Participants

6

Reactant 5

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 884332,4,4,6-Tetrabromocyclohexa-2,5-dienoneHCID 202826161-(2,4-Dichlorophenyl)prop-2-en-1-olHCID 202826771-(2,4-Dichlorophenyl)prop-2-en-1-one

Product 1

HCID 536940332,4-Dichloro-beta-(1-imidazolyl)propiophenone

Procedure

7.0 g. of 2,4-dichlorophenyl vinyl ketone (prepared by Jones oxidation of 2,4-dichlorophenyl vinyl carbinol using the general method described in J. Chem. Soc. (C), 1966, p. 1972) in 350 ml. of anhydrous ether was treated with 3.5 g. of imidazole, the solution stirred overnight and then washed with water (3 × 30 ml.). The solution is dried (MgSO4) and evaporated to give 2,4-dichloro-β-(1-imidazolyl)propiophenone as an amber gum (8.65 g.). The hydrochloride salt may be precipitated from ether and recrystallized from methanol/acetone as colorless rods, m.p. 105.5°-110° C.

Workup

  1. washwashed with water (3 × 30 ml.)
  2. dry with materialThe solution is dried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-2b1a10289aac4060948347073ffdb68f
Source dataset
uspto-grants-1977_08
Patent number
US04045568

Reaction notes

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