Dimethylformamide → Methyl 3-(2-(2-hydroxyethyl)-1H-imidazol-5-yl)-4-methylbenzoate

HRID 1488007Notes

Reaction equation

HRID 1488007 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:8]([O:10][CH3:11])=[O:9])=O.[C:16]([O-:19])([O-])=O.[K+].[K+].Cl.OCC[CH2:26][C:27](=[NH:30])OC.C[N:32](C)C=O>>[OH:19][CH2:16][CH2:26][C:27]1[NH:30][C:3]([C:5]2[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=2[CH3:15])[C:8]([O:10][CH3:11])=[O:9])=[CH:2][N:32]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 90021025Methyl 3-hydroxypropanecarboximidate hydrochloride2×HCID 90021973Methyl 3-(2-bromoacetyl)-4-methylbenzoate2×

Product 1

HCID 90030129Methyl 3-(2-(2-hydroxyethyl)-1H-imidazol-5-yl)-4-methylbenzoateYield 21%

Conditions

Temperature
80 °C

Procedure

Into a 250-mL round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a solution of methyl 3-(2-bromoacetyl)-4-methylbenzoate (compound 27.2, 10 g, 36.89 mmol) in N,N-dimethylformamide (150 mL). K2CO3 (30 g, 215.5 mmol) and 3-hydroxypropanimidamide hydrochloride (compound 23.1, 15 g, 120.4 mmol) were added to the reaction. The reaction mixture was stirred for 12 h at 80° C., then concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (2:1) as eluent to furnish 2 g (21%) of the title compound as a light yellow oil.

Workup

  1. customInto a 250-mL round-bottom flask, which was purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (2:1) as eluent

Sources & evidence

ORD record
ord-cab364ede8f9440fa7921dd1a26e63c7
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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