4-Cyanobenzoyl chloride → HCID 13491970, compound

HRID 1583542Notes

Reaction equation

HRID 1583542 reaction equation
[CH2:1]([C:3]1[NH:4][C:5](=[O:8])[NH:6][CH:7]=1)[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[C:13]([C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1)#[N:14]>[N+](C1C=CC=CC=1)([O-])=O>[C:13]([C:15]1[CH:23]=[CH:22][C:18]([C:19]([C:7]2[NH:6][C:5](=[O:8])[NH:4][C:3]=2[CH2:1][CH3:2])=[O:20])=[CH:17][CH:16]=1)#[N:14]

Participants

5

Reactant 3

HCID 801724-Cyanobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 155675284-ethyl-2,3-dihydro-1H-imidazol-2-one

Product 1

HCID 13491970HCID 13491970, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred mixture of 3.38 grams (0.03 mole) of 1,3-dihydro-4-ethyl-2H-imidazol-2-one, 13.3 grams (0.1 mole) of anhydrous aluminum chloride and 50 ml of nitrobenzene is added 5.0 grams (0.03 mole) of 4-cyanobenzoyl chloride. The mixture is stirred at 80° C. for 6 hours, then poured on 500 grams of ice. The resulting precipitate is washed with diethyl ether and water and is recrystallized from 500 ml ethyl alcohol to give 4.76 grams of the title compound. M.P. 269-271° C.

Workup

  1. washThe resulting precipitate is washed with diethyl ether and water
  2. customis recrystallized from 500 ml ethyl alcohol

Sources & evidence

ORD record
ord-e11bfd9d7a894aefb918284b289776d1
Source dataset
uspto-grants-1985_11
Patent number
US04552880

Reaction notes

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