Hydrochloric Acid → HCID 12970211, compound

HRID 1351014Notes

Reaction equation

HRID 1351014 reaction equation
C([O:3][C:4](=[O:33])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][N:15]2[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:18]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:17]=[C:16]2[CH3:32])=[CH:7][CH:6]=1)C.[OH-].[Na+].Cl>CCO.O>[CH3:32][C:16]1[N:15]([CH2:14][CH2:13][CH2:12][O:11][C:8]2[CH:7]=[CH:6][C:5]([C:4]([OH:33])=[O:3])=[CH:10][CH:9]=2)[C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:18]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:17]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59926127HCID 59926127, compound

Product 1

HCID 12970211HCID 12970211, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

(Scheme 2 (I)) To a solution of 4-[3-(2-Methyl-4,5-diphenyl-imidazol-1-yl)-propoxy]-benzoic acid ethyl ester (0.80 g, 1.8 mmol) in EtOH (20 mL) was added NaOH (10 N, 4.0 mL, 40.0 mmol). The resulting mixture was stirred at rt for 3 hours, diluted with water, acidified to pH˜1 using 1N HCl, extracted by CH2Cl2, and then was dried over MgSO4. After filtration and concentration in vacuo, the residue was purified by flash chromatography (SiO2: MeOH/CH2Cl2). This compound was obtained as a white dry foam in HCl salt form (0.80 g, 1.8 mmol, 99% yield): 1H NMR (DMSO): δ1.93 (m, 2H), 2.67 (s, 3H), 3.97 (t, 2H), 4.13 (t, 2H), 6.85 (d, J=8.82 mHz, 2H), 7.33 (s, 5H), 7.43 (m, 2H), 7.55 (m, 3H), 7.86 (d, J=8.82 mHz, 2H), 12.64 (b, 1H).

Workup

  1. extractionextracted by CH2Cl2
  2. dry with materialwas dried over MgSO4
  3. filtrationAfter filtration and concentration in vacuo
  4. customthe residue was purified by flash chromatography (SiO2: MeOH/CH2Cl2)
  5. customThis compound was obtained as
  6. dry with materiala white dry foam in HCl salt form (0.80 g, 1.8 mmol, 99% yield)

Sources & evidence

ORD record
ord-7e543df3c29e4697b73a57aaa29eb7d0
Source dataset
uspto-grants-2007_05
Patent number
USRE039634E1

Reaction notes

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