Triethylamine → (2,6-Dichlorophenyl)(2-methyl-1H-imidazol-1-yl)methanone

HRID 1903557Notes

Reaction equation

HRID 1903557 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.C(N(CC)CC)C.[Cl:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:16]=1[C:17](Cl)=[O:18]>O1CCCC1>[Cl:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:16]=1[C:17]([N:3]1[CH:4]=[CH:5][N:6]=[C:2]1[CH3:1])=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 127492-MethylimidazoleHCID 783922,6-Dichlorobenzoyl chloride

Product 1

HCID 13398629(2,6-Dichlorophenyl)(2-methyl-1H-imidazol-1-yl)methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

20.5 g of 2-methylimidazole and 25.3 g of triethylamine are dissolved in 200 ml of tetrahydrofuran. To this solution are added dropwise, within 15 minutes at reflux temperature, 52.4 g of 2,6-dichlorobenzoyl chloride (dissolved in 100 ml of tetrahydrofuran). The mixture is refluxed for 30 minutes, and subsequently freed from triethylamine hydrochloride by filtration in vacuo. The filtrate is concentrated to dryness in a rotary evaporator and the residue is recrystallised from 130 ml of acetonitrile. The crystals are filtered off with suction, washed with acetonitrile, and dried at 60° C. in vacuo to thus obtain 46.0 g (72.2% of theory) of the product, m.p. 116°-119° C.

Workup

  1. additionTo this solution are added dropwise, within 15 minutes
  2. temperatureThe mixture is refluxed for 30 minutes
  3. filtrationsubsequently freed from triethylamine hydrochloride by filtration in vacuo
  4. concentrationThe filtrate is concentrated to dryness in a rotary evaporator
  5. customthe residue is recrystallised from 130 ml of acetonitrile
  6. filtrationThe crystals are filtered off with suction
  7. washwashed with acetonitrile
  8. customdried at 60° C. in vacuo to thus obtain 46.0 g (72.2% of theory) of the product, m.p. 116°-119° C.

Sources & evidence

ORD record
ord-6fc4512154f5445b870e4cc707886839
Source dataset
uspto-grants-1984_03
Patent number
US04436892

Reaction notes

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