Sodium Hydroxide → HCID 21938126, compound

HRID 2054654Notes

Reaction equation

HRID 2054654 reaction equation
[C:1]1([N:7]2[C:11]3[CH:12]=[C:13]([O:16][CH:17](O)[CH3:18])[CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:26]([O:30][C:31](=[O:34])[CH:32]=[CH2:33])([CH3:29])([CH3:28])[CH3:27].[OH-:35].[Na+]>C1(C)C=CC=CC=1.O1CCCC1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:26]([O:30][C:31](=[O:34])[CH2:32][CH2:33][O:35][CH2:18][CH2:17][O:16][C:13]1[CH:14]=[CH:15][C:10]2[N:9]=[C:8]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:11]=2[CH:12]=1)([CH3:29])([CH3:28])[CH3:27]

Participants

8

Reactant 3

HCID 14798Sodium HydroxideHCID 15458tert-Butyl acrylate2×HCID 21938093HCID 21938093, compound

Product 1

HCID 21938126HCID 21938126, compound

Reagents, catalysts & solvents 4

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst2×HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.2 g of [(1,2-diphenyl-1H-benzimidazol-6-yl)oxy]ethan-1-ol was suspended in 1.7 ml of toluene and 0.7 ml of tetrahydrofuran. 60 μl of acrylic acid-tert-butyl ester, 13 mg of tetrabutylammonium hydrogen sulfate, and 1.45 ml of 32% sodium hydroxide solution were added to it, and it was allowed to stir for 48 hours. Another 60 μl of acrylic acid-tert-butyl ester and 13 mg of tetrabutylammonium hydrogen sulfate were added, and the mixture was left for 48 hours in an ultrasound bath. Then, it was diluted with water and extracted three times with toluene. The combined organic phases were washed with water and saturated sodium chloride solution, dried on sodium sulfate and concentrated by evaporation in a vacuum. The residue was chromatographed on silica gel.

Workup

  1. waitthe mixture was left for 48 hours in an ultrasound bath
  2. extractionextracted three times with toluene
  3. washThe combined organic phases were washed with water and saturated sodium chloride solution
  4. customdried on sodium sulfate
  5. concentrationconcentrated by evaporation in a vacuum
  6. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-b5b2c4e7371a4d3e8608e6d0ca43cb57
Source dataset
uspto-grants-2008_02
Patent number
US07329679B2

Reaction notes

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