Methanol → HCID 178500031, compound

HRID 1624257Notes

Reaction equation

HRID 1624257 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])[N:3]=[CH:2]1.OS(O)(=O)=O.[CH3:16]O>>[CH3:16][O:9][C:8](=[O:10])[CH2:7][CH2:6][C:4]1[N:3]=[CH:2][NH:1][CH:5]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 178525356HCID 178525356, compound

Product 1

HCID 178500031HCID 178500031, compoundYield 90%

Procedure

A solution of 3-(1H-imidazol-4-yl)-propionic acid (1.95 g, 13.9 mmol) and H2SO4 (catalytic) in MeOH (30 mL) was heated at reflux for 15 h, then concentrated in vacuo. The residue was dissolved in CH2Cl2 (40 mL) and washed with saturated NaHCO3(aq) (30 mL). The aqueous phase was saturated with sodium chloride and extracted with EtOAc (4×25 mL). The combined organic phases were dried (MgSO4) and concentrated in vacuo to give a yellow oil (1.93 g, 90%). 1H NMR (CDCl3) δ 2.68 (t, 2H, J=7.2 Hz), 2.93 (t, 2H, J=7.2 Hz), 3.69 (s, 3H), 6.81 (s, 1H), 7.55 (s, 1H).

Workup

  1. temperatureat reflux for 15 h
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in CH2Cl2 (40 mL)
  4. washwashed with saturated NaHCO3(aq) (30 mL)
  5. extractionextracted with EtOAc (4×25 mL)
  6. dry with materialThe combined organic phases were dried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-743a53bb86554e78bb504f1974cdd407
Source dataset
uspto-grants-2014_07
Patent number
US08778967B2

Reaction notes

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