Sodium Hydroxide → HCID 22613811, compound

HRID 1533057Notes

Reaction equation

HRID 1533057 reaction equation
C1C2C(=CC=CC=2)C=CC=1C([O:13][CH2:14][CH2:15][CH:16]([C:35]1[CH:40]=[CH:39][C:38]([Cl:41])=[C:37]([Cl:42])[CH:36]=1)[CH2:17][N:18]1[CH:22]=[CH:21][N:20]=[C:19]1[C:23]([C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=1)=[O:24])=O.[OH-].[Na+]>O1CCOCC1>[Cl:42][C:37]1[CH:36]=[C:35]([CH:16]([CH2:17][N:18]2[CH:22]=[CH:21][N:20]=[C:19]2[C:23]([C:25]2[CH:34]=[CH:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=2)=[O:24])[CH2:15][CH2:14][OH:13])[CH:40]=[CH:39][C:38]=1[Cl:41]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22613842HCID 22613842, compound

Product 1

HCID 22613811HCID 22613811, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-(3,4-Dichlorophenyl)-4-[2-(2-naphthoyl)imidazol-1-yl]butyl 2-naphthoate (1.25 g) (see Preparation 42) was dissolved in 1,4-dioxane (15 ml), 1N aqueous sodium hydroxide solution (4 ml) added and the mixture stiffed at room temperature overnight. The dioxane was then removed under reduced pressure and the residue partitioned between ethyl acetate and water. The organic phase was separated, washed sequentially with 1N aqueous sodium hydroxide solution, water and brine and the solvent removed under reduced pressure to give the crude product which was chromatographed on silica gel eluting with a solvent gradient of 99:1 changing to 95:5, by volume, dichloromethane:methanol, to give 3-(3,4-dichlorophenyl)-4-[2-(2-naphthoyl)imidazol-1-yl]butan-1-ol (0.8 g) as a gum.

Workup

  1. customThe dioxane was then removed under reduced pressure
  2. customthe residue partitioned between ethyl acetate and water
  3. customThe organic phase was separated
  4. washwashed sequentially with 1N aqueous sodium hydroxide solution, water and brine
  5. customthe solvent removed under reduced pressure
  6. customto give the crude product which
  7. customwas chromatographed on silica gel eluting with a solvent gradient of 99:1 changing to 95:5, by volume, dichloromethane

Sources & evidence

ORD record
ord-beb1ea5929124cd5919ac4128704fcf9
Source dataset
uspto-grants-2001_03
Patent number
US06207678B1

Reaction notes

Loading…