Sodium Hydroxide → HCID 178509595, compound

HRID 1468191Notes

Reaction equation

HRID 1468191 reaction equation
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][C:11]2[NH:12][CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=3)[N:15]=2)[CH:5]=1.C(C1C=CC(C2N=C(CC3C=C(C=CC=3)C(N)=O)NC=2)=CC=1)#N.[OH-].[Na+]>C1COCC1.CO>[C:22]([C:19]1[CH:18]=[CH:17][C:16]([C:14]2[N:15]=[C:11]([CH2:10][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:24])=[O:2])[NH:12][CH:13]=2)=[CH:21][CH:20]=1)#[N:23]

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 178497711HCID 178497711, compoundHCID 178509594HCID 178509594, compound

Product 1

HCID 178509595HCID 178509595, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Dissolve the mixture of crude 3-[4-(4-cyano-phenyl)-1H-imidazol-2-ylmethyl]-benzoic acid methyl ester and 3-[4-(4-cyano-phenyl)-1H-imidazol-2-ylmethyl]-benzamide (0.13 g) into 5 mL of 1:1 THF/MeOH. To this add 0.5 mL of 15% NaOH. Stir the mixture at room temperature for 2 h. Add 1 mL of 15% NaOH and stir an additional 2 h. Concentrate to dryness. Dissolve the residue into 5 mL of H2O and make acidic by the addition of 5% HCl. Extract with 3×10 mL of CH2Cl2 and dry with MgSO4. Concentrate to give 0.13 g of crude 3-[4-(4-cyano-phenyl)-1H-imidazol-2-ylmethyl]-benzoic acid and 3-[4-(4-cyano-phenyl)-1H-imidazol-2-ylmethyl]-benzamide as a purple residue.

Workup

  1. dissolutionDissolve
  2. stirringstir an additional 2 h
  3. concentrationConcentrate to dryness
  4. dissolutionDissolve the residue into 5 mL of H2O
  5. additionmake acidic by the addition of 5% HCl
  6. extractionExtract with 3×10 mL of CH2Cl2
  7. dry with materialdry with MgSO4
  8. concentrationConcentrate

Sources & evidence

ORD record
ord-c0a54d781a7e41df88b92f15981e33dc
Source dataset
uspto-grants-2015_04
Patent number
US09000154B2

Reaction notes

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