Sodium Hydroxide → HCID 22066070, compound

HRID 2101704Notes

Reaction equation

HRID 2101704 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:21]([O:23]CC3C=CC=CC=3)=[O:22])[N:11]([CH3:20])[C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([C:21]([OH:23])=[O:22])[N:11]([CH3:20])[C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10181533HCID 10181533, compound

Product 1

HCID 22066070HCID 22066070, compoundYield 102.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of benzyl 4,5-di-(4-chlorophenyl)-1-methylimidazole-2-carboxylate (185 mg, 0.42 mmol) from Example 19, Step C in methanol (20 mL) was added aq. 5N sodium hydroxide (0.25 mL, 1.27 mmol). The reaction was stirred at rt for 20 hr, concentrated in vacuo, acidified with 2N hydrochloric acid (0.50 mL), and extracted twice with ethyl acetate. The organic layers were washed with brine, dried over sodium sulfate, and evaporated to dryness to afford the crude title acid (150 mg) as a mixture with decarboxylated material. This material was used directly in Step B.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted twice with ethyl acetate
  3. washThe organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-e247e60f0a5d4a4e952829391d75410a
Source dataset
uspto-grants-2009_08
Patent number
US07572785B2

Reaction notes

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