2-Chlorophenol → Ammonium Hydroxide

HRID 379043Notes

Reaction equation

HRID 379043 reaction equation
Br.[C:2]([C:4]1[CH:20]=[CH:19][C:7]([CH2:8][N:9]2[C:13]([CH2:14][O:15][C:16](=[O:18])[CH3:17])=[CH:12][N:11]=[CH:10]2)=[CH:6][C:5]=1F)#[N:3].[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[OH:29].C(=O)([O-])[O-:31].[Cs+].[Cs+]>CN(C=O)C>[ClH:22].[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[O:29][C:5]1[CH:6]=[C:7]([CH:19]=[CH:20][C:4]=1[C:2]#[N:3])[CH2:8][N:9]1[C:13]([CH2:14][O:15][C:16](=[O:18])[CH3:17])=[CH:12][N:11]=[CH:10]1.[NH4+:3].[OH-:31]

Participants

6

Reactant 3

HCID 72452-ChlorophenolHCID 10796Cesium carbonateHCID 18535996HCID 18535996, compound

Product 2

HCID 14923Ammonium HydroxideHCID 70242620Acetic Acid 3-[3-(2-chloro-phenoxy)-4-cyano-benzyl]-3H-imidazol-4-ylmethyl Ester Hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 1-(4-cyano-3-fluorobenzyl)-5-(acetoxymethyl)-imidazole hydrobromide (0.29 g, 1.06 mmol) in DMF (7.0 mL) was added 2-chlorophenol (0.132 mL, 1.27 mmol) and cesium carbonate (0.691 g, 2.12 mmol). The mixture was heated to 55° C. and stirred for 18 hr. The DMF was removed in vacuo and the residue was partitioned with EtOAc and saturated NaHCO3 solution. The EtOAc layer was washed with H2O, brine, and dried (MgSO4). Filtration and concentration to dryness gave the title compound after chromatography (SiO2, CH2Cl2:CH3OH: NH4OH/98:2:0.2) and conversion to the hydrochloride salt.

Workup

  1. customThe DMF was removed in vacuo
  2. customthe residue was partitioned with EtOAc and saturated NaHCO3 solution
  3. washThe EtOAc layer was washed with H2O, brine
  4. dry with materialdried (MgSO4)
  5. filtrationFiltration and concentration to dryness

Sources & evidence

ORD record
ord-ef18ad889378407694c8594eba0f2979
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

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