Sodium Hydroxide → HCID 86601227, compound

HRID 349273Notes

Reaction equation

HRID 349273 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[N:8]=[CH:9][N:10]([CH2:18][C:19]2[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([C:29]([F:32])([F:31])[F:30])[CH:20]=2)[C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:6]>CCO>[F:32][C:29]([F:30])([F:31])[C:21]1[CH:20]=[C:19]([CH:24]=[C:23]([C:25]([F:26])([F:27])[F:28])[CH:22]=1)[CH2:18][N:10]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:7]([C:5]([OH:6])=[O:4])[N:8]=[CH:9]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86601228HCID 86601228, compound

Product 1

HCID 86601227HCID 86601227, compoundYield 1,100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Add 5N NaOH (200 mL) to a solution of 1-(3,5-bis-trifluoromethyl-benzyl)-5-phenyl-1H-imidazole-4-carboxylic acid methyl ester (3.0 g, 7.0 mmol) in EtOH (200 mL). Warm the mixture to 70° C. and stir for 16 h. Then cool to RT and concentrate to 220 mL under reduced pressure. Cool this solution to 0° C. and add conc. HCl to pH 1. Filter the resulting precipitate and dry under vacuum to provide 3.0 g (1100%) of the title compound as a light brown solid. 1H NMR (300 MHz, DMSO-d6) δ 7.95 (s, 1H), 7.85 (s, 1R), 7.19–7.34 (m, SR), 7.15–7.02 (m, 2R), 5.20 (s, 2R), 3.20 (br s, 11H); MS/ES 415.2 (M+1).

Workup

  1. temperatureThen cool to RT
  2. concentrationconcentrate to 220 mL under reduced pressure
  3. temperatureCool this solution to 0° C.
  4. additionadd conc. HCl to pH 1
  5. filtrationFilter the resulting precipitate
  6. customdry under vacuum

Sources & evidence

ORD record
ord-3a26b81ab5f64e588991c4643b970e7a
Source dataset
uspto-grants-2007_02
Patent number
US07179804B2

Reaction notes

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