Sodium Hydroxide → HCID 69135049, compound

HRID 969496Notes

Reaction equation

HRID 969496 reaction equation
[OH:1][C:2]1[C:7]2[N:8]=[C:9]([CH3:12])[N:10]([CH3:11])[C:6]=2[CH:5]=[C:4]([N:13]([CH3:17])[C:14](=[O:16])[CH3:15])[C:3]=1[CH2:18][CH2:19][CH:20](O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[OH-].[Na+]>>[CH3:12][C:9]1[N:10]([CH3:11])[C:6]2[CH:5]=[C:4]([N:13]([CH3:17])[C:14](=[O:16])[CH3:15])[C:3]3[CH2:18][CH2:19][CH:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[O:1][C:2]=3[C:7]=2[N:8]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 69134261HCID 69134261, compound

Product 1

HCID 69135049HCID 69135049, compoundYield 57%

Conditions

Temperature
80 °C

Procedure

A suspension of 0.75 g (2.0 mmol) N-[7-hydroxy-6-(3-hydroxy-3-phenyl-propyl)-2,3-dimethyl-3H-benzoimidazol-5-yl]-N-methyl-acetamide in 8 ml 85% orthcphosphodc acid was heated to 80° C. After 2 h stirring, the reaction was cooled to room temperature, neutralized with 6M sodium hydroxide and extracted with ethyl acetate (3×20 ml). The organic layers were dried over magnesium sulphate and concentrated in vacuo. The residue was crystallized from ethyl acetate/disopropyl ether (1:10) to afford the title compound (57%) as a beige solid. m.p. 214°-216° C.

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. extractionextracted with ethyl acetate (3×20 ml)
  3. dry with materialThe organic layers were dried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe residue was crystallized from ethyl acetate/disopropyl ether (1:10)

Sources & evidence

ORD record
ord-9a2a9da37a564923afcadae4e0d174f5
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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