3,4-Dichlorobenzyl chloride → HCID 20376128, compound

HRID 2052535Notes

Reaction equation

HRID 2052535 reaction equation
CC(C)([O-])C.[K+].[NH:7]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:10]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:9]=[CH:8]1.[Cl:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][C:30]=1[Cl:31])[CH2:26]Cl>CN(C)C=O>[Cl:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][C:30]=1[Cl:31])[CH2:26][N:7]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:10]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:9]=[CH:8]1

Participants

5

Reactant 3

HCID 76093,4-Dichlorobenzyl chlorideHCID 350670Diethyl 1H-imidazole-4,5-dicarboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 20376128HCID 20376128, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium t-butoxide (10.9 g) was added with stirring to a solution of diethyl imidazole-4,5-dicarboxylate (20 g, described by Jones, J.A.C.S. 74, 1085 (1952)) in dry dimethylformamide (300 ml) at room temperature and the mixture was stirred for 40 minutes. 3,4-Dichlorobenzyl chloride (20.4 g) was added and the mixture was heated at reflux for 11 hours. The cooled reaction mixture was poured into ice-water (500 ml) and extracted with chloroform (2×200 ml). The combined extracts were washed with water (3×300 ml), dried over magnesium sulphate, filtered and evaporated to dryness. The solid residue was crystallised from methanol (100 ml) to give diethyl 1-(3,4-dichlorobenzyl)imidazole-4,5-dicarboxylate, m.p. 105°-107° C., (13 g) as a colourless solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 11 hours
  3. customThe cooled reaction mixture
  4. extractionextracted with chloroform (2×200 ml)
  5. washThe combined extracts were washed with water (3×300 ml)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe solid residue was crystallised from methanol (100 ml)

Sources & evidence

ORD record
ord-663b64fda502423e99f0995fb1243c8a
Source dataset
uspto-grants-1980_01
Patent number
US04185992

Reaction notes

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