Sodium Hydroxide → HCID 18976091, compound

HRID 2393509Notes

Reaction equation

HRID 2393509 reaction equation
C1(S([N:10]2[C:22]3[CH:21]=[C:20]([CH:23]([N:25]4[CH:29]=[CH:28][N:27]=[CH:26]4)[CH3:24])[CH:19]=[CH:18][C:17]=3[C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=3)(=O)=O)C=CC=CC=1.[OH-].[Na+]>C(O)C>[N:25]1([CH:23]([C:20]2[CH:19]=[CH:18][C:17]3[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[NH:10][C:22]=3[CH:21]=2)[CH3:24])[CH:29]=[CH:28][N:27]=[CH:26]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18976099HCID 18976099, compound

Product 1

HCID 18976091HCID 18976091, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixed solution of the thus obtained 9-benzenesulfonyl-2-[1-(1H-imidazol-1-yl)ethyl]carbazole (0.436 g, 1.09 mmol), ethanol (50 ml) and 2N sodium hydroxide aqueous solution (10 ml) was heated under reflux for 4 hours. After evaporation of volatile components under reduced pressure, the resulting residue was mixed with chloroform and washed with saturated sodium chloride aqueous solution, and the organic layer was dried over magnesium sulfate. After evaporation of the solvent under reduced pressure, the resulting residue was purified by silica gel column chromatography to obtain crude crystals from the eluate of chloroform-methanol (100:1). By recrystallizing the crude crystals from ethyl acetate, 0.174 g of 2-[1-(1H-imidazol-1-yl) ethyl]carbazole was obtained.

Workup

  1. temperatureunder reflux for 4 hours
  2. customAfter evaporation of volatile components under reduced pressure
  3. additionthe resulting residue was mixed with chloroform
  4. washwashed with saturated sodium chloride aqueous solution
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. customAfter evaporation of the solvent under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography
  8. customto obtain crude crystals from the eluate of chloroform-methanol (100:1)
  9. customBy recrystallizing the crude crystals from ethyl acetate

Sources & evidence

ORD record
ord-12982eaaa2a242c899164f48341e2425
Source dataset
uspto-grants-1998_09
Patent number
US05807880

Reaction notes

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