Hydrochloric Acid → Methyl 4-[2-(imidazol-2-yl)ethyl]benzoate hydrochloride

HRID 583686Notes

Reaction equation

HRID 583686 reaction equation
[C:1]([CH2:3][CH2:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1)#[N:2].CO.[ClH:17].CO[CH:20](OC)[CH2:21][NH2:22]>CCOCC>[ClH:17].[NH:2]1[CH:20]=[CH:21][N:22]=[C:1]1[CH2:3][CH2:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 89728Aminoacetaldehyde dimethyl acetalHCID 13308299Methyl 4-(2-cyanoethyl)benzoate

Product 1

HCID 18928585Methyl 4-[2-(imidazol-2-yl)ethyl]benzoate hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Nitrile 23-3 (400 mg, 2.11 mmol) was dissolved in 10 mL Et2O at 0° MeOH (289 μL, 4.2 mmol) was added, the mixture was saturated with anhydrous HCl. Once the white ppt. formed, the solvent was evaporated and replaced with MeOH (5 mL), cooled to 0°, and aminoacetaldehyde dimethylacetal (250 μL, 2.3 mmol) was added. The reaction was heated to reflux for 3 days then concentrated, diluted in 10 mL 6N HCl and concentrated again providing 23-4 as a solid.

Workup

  1. additionwas added
  2. customformed
  3. customthe solvent was evaporated
  4. temperaturecooled to 0°
  5. temperatureThe reaction was heated
  6. temperatureto reflux for 3 days
  7. concentrationthen concentrated
  8. additiondiluted in 10 mL 6N HCl
  9. concentrationconcentrated again

Sources & evidence

ORD record
ord-d853fbbf2d42476e87b82191a538b8ab
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Reaction notes

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