Imidazole → HCID 2995961, compound

HRID 2232319Notes

Reaction equation

HRID 2232319 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].Cl[CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=1>CN(C)C=O>[N+:18]([C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=1)[O:11][CH2:10][CH2:9][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 43044241-(2-chloroethoxy)-3-nitrobenzene

Product 1

HCID 2995961HCID 2995961, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After dissolving 3.74 g. of imidazole in 60 ml. of dry N,N-dimethylformamide, 1.78 g. of 50% sodium hydride in oil was added. When the effervescence had stopped (circa 1 hr.), 7.35 g. of 1-(2-chloroethoxy)-3-nitrobenzene was added. After stirring overnight, the reaction was concentrated under vacuum. Water was added to the residue and the product was extracted into chloroform. The product was extracted out of the chloroform layer with dilute hydrochloric acid. Next, the aqueous acid layer was neutralized with potassium carbonate and the oily product extracted into chloroform. Upon drying the chloroform extract with sodium sulfate, it was concentrated under vacuum to an oil which crystallized on standing. Recrystallization from isopropyl acetate gave 6.12 g. of product as the monohydrate, m.p. 52.5°-55.5° C.

Workup

  1. dissolutionAfter dissolving 3.74 g
  2. custom(circa 1 hr.), 7.35 g
  3. concentrationthe reaction was concentrated under vacuum
  4. additionWater was added to the residue
  5. extractionthe product was extracted into chloroform
  6. extractionThe product was extracted out of the chloroform layer with dilute hydrochloric acid
  7. extractionthe oily product extracted into chloroform
  8. dry with materialUpon drying the chloroform
  9. extractionextract with sodium sulfate, it
  10. concentrationwas concentrated under vacuum to an oil which
  11. customcrystallized
  12. customRecrystallization from isopropyl acetate
  13. customgave 6.12 g

Sources & evidence

ORD record
ord-4f410fe78b0441b7a9bc81528eb72e96
Source dataset
uspto-grants-1988_11
Patent number
US04788195

Reaction notes

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