Imidazole → HCID 22132903, compound

HRID 904145Notes

Reaction equation

HRID 904145 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.[NH:14]1[CH:18]=[CH:17][N:16]=[CH:15]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[N:14]1([CH2:3][C:4]2[CH:13]=[CH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH:18]=[CH:17][N:16]=[CH:15]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 10340Sodium CarbonateHCID 30838232-(Chloromethyl)quinoline hydrochloride

Product 1

HCID 22132903HCID 22132903, compoundYield 21.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture consisting of 2-chloromethylquinoline hydrochloride (10.0 g.), imidazole (3.2 g.) and sodium carbonate (14.8 g.) in N,N-dimethylformamide (100 ml.) was heated on a steam bath for a period of seven hours and then evaporated. The residue was taken up in chloroform and the resulting solution was filtered to give a clear filtrate. Evaporation of the latter liquid while under reduced pressure then gave a solid substance, which was subsequently crystallized from chloroform/petroleum ether (b.p. 60°-80° C.) and then recrystallized from diethyl ether to give pure 2-(1-imidazol-1-ylmethyl)quinoline (yield, 2.10 g.), m.p. 106°-107° C.

Workup

  1. temperaturewas heated on a steam bath for a period of seven hours
  2. customevaporated
  3. filtrationthe resulting solution was filtered
  4. customto give a clear filtrate
  5. customEvaporation of the latter liquid while under reduced pressure
  6. customthen gave a solid substance, which
  7. customwas subsequently crystallized from chloroform/petroleum ether (b.p. 60°-80° C.)
  8. customrecrystallized from diethyl ether

Sources & evidence

ORD record
ord-93ebaf2c8eb8416a9fd29ed426760058
Source dataset
uspto-grants-1980_10
Patent number
US04230714

Reaction notes

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