Diethyl Ether → HCID 12797102, compound

HRID 484702Notes

Reaction equation

HRID 484702 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][N:10]=[C:9]2[CH2:13][CH3:14])=[CH:4][CH:3]=1.[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1.C(OCC)C>C1(C)C=CC=CC=1>[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([N:8]3[CH:12]=[CH:11][N:10]=[C:9]3[CH2:13][CH3:14])=[CH:6][CH:7]=2)=[O:21])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 85014-Chlorobenzoyl chlorideHCID 12797132HCID 12797132, compound

Product 1

HCID 12797102HCID 12797102, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.9 g of 1-(4-aminophenyl)-2-ethylimidazole was added to a solution of 2.6 g of p-chlorobenzoyl chloride in 50 ml of toluene, and the mixture was refluxed with stirring for 7 hours. The reaction mixture was naturally cooled and diethyl ether was then added thereto. The precipitated crystal was recovered by filtration, washed sufficiently with ethyl ether and recrystallized from ethanol and then from water to obtain 2.5 g of the intended compound in the form of a hydrochloride. The melting point was 265° to 267° C. Elementary analysis values as C18H16ClN3O.HCl.1/2H2O were as follows.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureThe reaction mixture was naturally cooled
  3. filtrationThe precipitated crystal was recovered by filtration
  4. washwashed sufficiently with ethyl ether
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-a9435553479540c1828495401af3e1fd
Source dataset
uspto-grants-1985_08
Patent number
US04533669

Reaction notes

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