Triethylamine → 1-(triphenylmethyl)-1H-Imidazole-4-acetic acid methyl ester

HRID 2306192Notes

Reaction equation

HRID 2306192 reaction equation
Cl.[NH:2]1[CH:6]=[C:5]([CH2:7][C:8]([O:10][CH3:11])=[O:9])[N:4]=[CH:3]1.C(N(CC)CC)C.[C:19]1([C:25](Br)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C=O)C>[C:19]1([C:25]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:2]2[CH:6]=[C:5]([CH2:7][C:8]([O:10][CH3:11])=[O:9])[N:4]=[CH:3]2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11692BromotriphenylmethaneHCID 178499561HCID 178499561, compound

Product 1

HCID 105239671-(triphenylmethyl)-1H-Imidazole-4-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 4-imidazoleacetate hydrochloride, as described above in Step A, (4.30 g, 24.3 mmol) in dry DMF (50 mL) were added triethylamine (7.45 mL, 53.5 mmol), then triphenylmethyl bromide (8.64 g, 26.7 mmol). The mixture was stirred at ambient temperature for 18 hours, then partitioned between H2O (250 mL) and EtOAc (250 mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica, eluting with EtOAc, to yield the product as a pale solid.

Workup

  1. custompartitioned between H2O (250 mL) and EtOAc (250 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica
  6. washeluting with EtOAc

Sources & evidence

ORD record
ord-797c492c52f74987a2af259a3cf321f9
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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