Sodium Hydroxide → (+/-)-4-Dodecyl-alpha-phenyl-1H-imidazole-1-acetic acid

HRID 2380504Notes

Reaction equation

HRID 2380504 reaction equation
[OH-].[Na+].[CH2:3]([C:15]1[N:16]=[CH:17][N:18]([CH:20]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:21]([O:23]CC)=[O:22])[CH:19]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>C(O)C>[CH2:3]([C:15]1[N:16]=[CH:17][N:18]([CH:20]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:21]([OH:23])=[O:22])[CH:19]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10572975ethyl (+/-)-4-dodecyl-alpha-phenyl-1H-imidazole-1-acetate

Product 1

HCID 10642923(+/-)-4-Dodecyl-alpha-phenyl-1H-imidazole-1-acetic acidYield 60.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Solid NaOH (0.9 g, 22.6 mmol) was added to a solution of ethyl (±)-4-dodecyl-α-phenyl-1H-imidazole-1-acetate (4.5 g, 11.3 mmol) in 150 mL 95% ethanol. The resulting solution was stirred for 2 hours and then concentrated in vacuo. The residue was partitioned between water and ether, the aqueous layer was acidified with concentrated HCl, and extracted with dichloromethane. The dichloromethane solution was dried over MgSO4, filtered, and concentrated to give a white solid (2.53 g, 55%); mp 110°-118° C.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between water and ether
  3. extractionextracted with dichloromethane
  4. dry with materialThe dichloromethane solution was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3a38a7ea78b54284a9fc01b5cdbded96
Source dataset
uspto-grants-1994_11
Patent number
US05366987

Reaction notes

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