Hydrochloric Acid → HCID 53998100, compound

HRID 1017738Notes

Reaction equation

HRID 1017738 reaction equation
[Mg].Br[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:11]([N:18]1[C:22]([C:23](=[O:25])[CH3:24])=[CH:21][N:20]=[CH:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>O1CCCC1>[CH2:11]([N:18]1[C:22]([C:23]([OH:25])([CH2:3][CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH3:24])=[CH:21][N:20]=[CH:19]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7666Phenethyl bromideHCID 5462224MagnesiumHCID 116153681-(1-Benzyl-1H-imidazol-5-yl)ethan-1-one

Product 1

HCID 53998100HCID 53998100, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

1.0 g of magnesium turnings are covered with 5 ml of dry tetrahydrofuran. To the mixture is added 7.8 g of (2-bromoethyl)benzene in 30 ml of dry tetrahydrofuran at such a rate that a smooth reaction is maintained. The mixture is then heated under reflux for one hour. After being cooled to room temperature, 3.0 g of 1-(3-benzyl-3H-imidazol-4-yl)-ethanone in 20 ml of tetrahyrofuran is added dropwise to the Grignard reagent and the reaction mixture is refluxed for one hour. The cooled reaction mixture is poured into a cold dilute hydrochloric acid solution. Work-up of the mixture gives the crude product, which is recrystallized from ethyl acetate. The yield is 3.3 g.

Workup

  1. customthat a smooth reaction
  2. temperatureis maintained
  3. temperatureThe mixture is then heated
  4. temperatureunder reflux for one hour
  5. temperaturethe reaction mixture is refluxed for one hour
  6. customThe cooled reaction mixture

Sources & evidence

ORD record
ord-bb3ae9594bcf423095d9870f8c18eaff
Source dataset
uspto-grants-2002_11
Patent number
US06479530B2

Reaction notes

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