Imidazole → HCID 86740589, compound

HRID 1284534Notes

Reaction equation

HRID 1284534 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[N:12]1([CH2:17][CH2:18][OH:19])[CH:16]=[CH:15][N:14]=[CH:13]1.N1C=CN=C1.[C:25]1(=[O:30])[O:29]CCO1>C(#N)C.C(N(CC)CC)C>[C:25]([OH:29])(=[O:30])/[CH:7]=[CH:3]\[C:4]([OH:19])=[O:5].[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:19][CH2:18][CH2:17][N:12]1[CH:16]=[CH:15][N:14]=[CH:13]1)=[O:5]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 7303Ethylene carbonateHCID 666452,4-Dichlorobenzoyl chlorideHCID 74168N-(2-Hydroxyethyl)imidazole

Product 1

HCID 86740589HCID 86740589, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

11 g (0.05 mol) of 2,4-dichlorobenzoyl chloride were added dropwise to a mixture of 5.5 g (0.05 mol) of 1H-imidazole -1-ethanol [prepared from imidazole and ethylene carbonate by the process of British patent No. 939,681], 20 ml of triethylamine and 150 ml of acetonitrile. The reaction mixture was kept at about 80° C. for another 1.5 hours and then the solvent was evaporated. The residue was dissolved in a mixture of ethyl acetate and diethyl ether and was then extracted with water and subsequently with dilute hydrochloric acid. The acidic aqueous layer was made alkaline after which the base was taken up in ethyl acetate. The organic layer was extracted three times with water, dried and partly concentrated by evaporation. The residue was acidified with maleic acid and the 2-(1H-imidazol-1-yl)-ethyl 2,4-dichlorobenzoate (Z)-2-butenedioate (1:1) obtained was crystallized from a mixture of 2-propanol, acetone and diethyl ether to obtain the product with a melting point of 116-117° C.

Workup

  1. customthe solvent was evaporated
  2. dissolutionThe residue was dissolved in a mixture of ethyl acetate and diethyl ether
  3. extractionwas then extracted with water and subsequently with dilute hydrochloric acid
  4. extractionThe organic layer was extracted three times with water
  5. customdried
  6. concentrationpartly concentrated by evaporation

Sources & evidence

ORD record
ord-c2c6c427f42c411f8e0e52550ba6d28d
Source dataset
uspto-grants-1986_01
Patent number
US04563473

Reaction notes

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