Acetic Acid → HCID 178470172, compound

HRID 241038Notes

Reaction equation

HRID 241038 reaction equation
[CH:1]1[C:6]([C:7]([CH2:9][NH2:10])=O)=[CH:5][CH:4]=[C:3]([Br:11])[CH:2]=1.Cl.C([O-])(=O)C.[Na+].C(O)(=O)C.[NH:22]=[C:23](SC)[C:24]([O:26][CH2:27][CH3:28])=[O:25].C([O-])(O)=O.[Na+]>O1CCOCC1>[Br:11][C:3]1[CH:4]=[CH:5][C:6]([C:7]2[N:22]=[C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[NH:10][CH:9]=2)=[CH:1][CH:2]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 27982162-Amino-1-(4-bromophenyl)ethan-1-one hydrochlorideHCID 10464471ethyl 2-imino-2-(methylthio)acetate

Product 1

HCID 178470172HCID 178470172, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 2-amino-4-bromoacetophenone hydrochloride (4.0 g, 16.0 mmol), sodium acetate (6.1 g, 90.0 mmol), acetic acid (4.6 mL, 80.0 mmol) and ethyl 2-imino-2-(methylthio)acetate (7.7 g, 32.0 mmol) in dioxane (40 mL) was stirred at 95° C. overnight. The reaction mixture was carefully neutralized with saturated NaHCO3 solution and extracted with ethyl acetate. The organic solution was dried over sodium sulfate and concentrated. Purification by silica gel column chromatography (ethyl acetate:hexanes 1:1) afforded ethyl 4-(4-bromophenyl)-1H-imidazole-2-carboxylate (3.53 g, 75.0%). MS (EI) for C12H11BrN2O2: 296 (MH+).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic solution was dried over sodium sulfate
  3. concentrationconcentrated
  4. customPurification by silica gel column chromatography (ethyl acetate:hexanes 1:1)

Sources & evidence

ORD record
ord-03495ac8991b40ca9c0851dbd5986bf2
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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