Methanol → HCID 178418812, compound

HRID 1875217Notes

Reaction equation

HRID 1875217 reaction equation
S(Cl)(Cl)=O.[Na].[C:6]([OH:9])(=[O:8])[CH3:7].[NH:10]1[CH:14]=[CH:13][N:12]=[CH:11]1.[CH3:15]O>>[NH:10]1[CH:14]=[C:13]([CH2:7][C:6]([O:9][CH3:15])=[O:8])[N:12]=[CH:11]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 68723503HCID 68723503, compound

Product 1

HCID 178418812HCID 178418812, compoundYield 84%

Procedure

Thionyl chloride (3 mL, 41.1 mmol) was added slowly over the course of 30 mins to a 0° C. solution of imidazole acetic acid sodium salt (1.84 g, 10.0 mmol) in MeOH (40 mL) and the solution was stirred at RT overnight and evaporated. Aqueous NH4OH was slowly added and the solution was extracted with 9:1 CH2Cl2:MeOH to provide the title compound (1.18 g, 84%) as a yellow oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.69 (d, J=5.22 Hz, 1H), 7.02 (br. s., 1H), 3.63-3.82 (m, 5H).

Workup

  1. customevaporated
  2. additionAqueous NH4OH was slowly added
  3. extractionthe solution was extracted with 9:1 CH2Cl2

Sources & evidence

ORD record
ord-8064c3179a384f2ea2f1fc9975765a62
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

Loading…