Hydrochloric Acid → HCID 178520541, compound

HRID 1017740Notes

Reaction equation

HRID 1017740 reaction equation
[Mg].Br[CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:12].[NH:13]1[CH:17]=[C:16]([CH:18]=[O:19])[N:15]=[CH:14]1.Cl>O1CCCC1>[Cl:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[CH2:5][CH2:4][CH2:3][CH:18]([C:16]1[N:15]=[CH:14][NH:13][CH:17]=1)[OH:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 764281H-Imidazole-4-carbaldehydeHCID 2941151-(3-Bromopropyl)-2-chlorobenzeneHCID 5462224Magnesium2×

Product 1

HCID 178520541HCID 178520541, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

3.3 g of magnesium turnings are covered with 40 ml of dry tetrahydrofuran. To the mixture is added 32.0 g of 1-(3-bromopropyl)-2-chlorobenzene (prepared according to Baddar, F. G. et al., J. Chem. Soc., 1959, 1027) in 100 ml of dry tetrahydrofuran at such a rate that a smooth reaction is maintained. When the magnesium turnings have reacted the solution is cooled to room temperature. 4.3 g of imidazole-4-carbaldehyde in 40 ml of dry tetrahydrofuran is then 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. Tetrahydrofuran is distilled off under reduced pressure and the residue is cooled. The resulting precipitate is filtered and washed with water. The crude product is recrystallized from ethanol. The yield is 8.0 g. Melting point of the hydrochloride salt is 152-154° C.

Workup

  1. customthat a smooth reaction
  2. temperatureis maintained
  3. temperaturethe reaction mixture is refluxed for one hour
  4. customThe cooled reaction mixture
  5. distillationTetrahydrofuran is distilled off under reduced pressure
  6. temperaturethe residue is cooled
  7. filtrationThe resulting precipitate is filtered
  8. washwashed with water
  9. customThe crude product is recrystallized from ethanol
  10. customis 152-154° C.

Sources & evidence

ORD record
ord-975bab69930f4de89a49915432b78b45
Source dataset
uspto-grants-2002_11
Patent number
US06479530B2

Reaction notes

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