Diethyl Ether → HCID 12797102, compound

HRID 1155288Notes

Reaction equation

HRID 1155288 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-4ffcae70933e4799912adbc56631e971
Source dataset
uspto-grants-1981_11
Patent number
US04301169

Reaction notes

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