Hydrochloric Acid → Ethyl 5-methyl-2-phenylimidazole-4-acetate

HRID 413969Notes

Reaction equation

HRID 413969 reaction equation
Cl.[C:2]([CH2:4][C:5]1[N:6]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:8][C:9]=1[CH3:10])#N.[OH2:17].[OH-].[Na+].[CH2:20]([OH:22])[CH3:21]>>[CH2:20]([O:22][C:2]([CH2:4][C:5]1[N:6]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:8][C:9]=1[CH3:10])=[O:17])[CH3:21]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 65475Mefenidil

Product 1

HCID 22597552Ethyl 5-methyl-2-phenylimidazole-4-acetate

Procedure

Hydrochloric acid in ethanol (35%, 150 ml) was added to 4-cyanomethyl-5-methyl-2-phenylimidazole (20.5 g) and heated to reflux temperature. After 1 h the reaction mixture was poured into water (400 ml) and NaOH was added (pH>8), followed by extraction with dichloromethane (3 times). The combined organic layers were dried over sodium sulfate and evaporated to dryness in vacuo.

Workup

  1. temperatureheated
  2. temperatureto reflux temperature
  3. additionwas added (pH>8)
  4. extractionfollowed by extraction with dichloromethane (3 times)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-992370299d9d4e1298eeaed20b74f565
Source dataset
uspto-grants-2003_05
Patent number
US06569863B1

Reaction notes

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