Sodium Hydroxide → 2-(2-Chloro-phenoxy)-4-(5-hydroxymethyl-imidazol-1-ylmethyl)-benzonitrile Hydrochloride

HRID 379044Notes

Reaction equation

HRID 379044 reaction equation
Cl.[Cl:2][C:3]1[CH:28]=[CH:27][CH:26]=[CH:25][C:4]=1[O:5][C:6]1[CH:7]=[C:8]([CH:20]=[CH:21][C:22]=1[C:23]#[N:24])[CH2:9][N:10]1[C:14]([CH2:15][O:16]C(=O)C)=[CH:13][N:12]=[CH:11]1.[OH-].[Na+]>C1COCC1>[ClH:2].[Cl:2][C:3]1[CH:28]=[CH:27][CH:26]=[CH:25][C:4]=1[O:5][C:6]1[CH:7]=[C:8]([CH2:9][N:10]2[C:14]([CH2:15][OH:16])=[CH:13][N:12]=[CH:11]2)[CH:20]=[CH:21][C:22]=1[C:23]#[N:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70242620Acetic Acid 3-[3-(2-chloro-phenoxy)-4-cyano-benzyl]-3H-imidazol-4-ylmethyl Ester Hydrochloride

Product 1

HCID 216970452-(2-Chloro-phenoxy)-4-(5-hydroxymethyl-imidazol-1-ylmethyl)-benzonitrile Hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of acetic acid 3-[3-(2-chloro-phenoxy)-4-cyano-benzyl]-3H-imidazol-4-ylmethyl ester hydrochloride (as described in Example 14)(0.112 g, 0.268 mmol) in THF (2.0 mL) was added 1M NaOH (0.536 mL). After 3.5 hr. the reaction was partitioned between EtOAc and saturated NaHCO3 solution. The EtOAc layer was washed with H2O, brine, and dried (MgSO4). Filtration and concentration in vacuo gave the title compound after conversion to the hydrochloride salt.

Workup

  1. customthe reaction was partitioned between EtOAc and saturated NaHCO3 solution
  2. washThe EtOAc layer was washed with H2O, brine
  3. dry with materialdried (MgSO4)
  4. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-d6d7220714534049a66a876c87f539c1
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

Loading…