Imidazole → Imidazol-1-YL-oxo-acetic acid tert-butyl ester

HRID 1955731Notes

Reaction equation

HRID 1955731 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].[C:6](Cl)(=[O:10])[C:7](Cl)=[O:8].[NH:12]1[CH:16]=[CH:15][N:14]=[CH:13]1>C1COCC1>[N:12]1([C:6](=[O:10])[C:7]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:8])[CH:16]=[CH:15][N:14]=[CH:13]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 6386tert-ButanolHCID 65578Oxalyl chloride

Product 1

HCID 11217804Imidazol-1-YL-oxo-acetic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

58.5 g (0.79 mol) of tert-butanol are added with stirring at 0° C. under argon to 100 g (0.79 mol) of oxalyl chloride in 1.3 l of THF. After stirring at 0° C for 1 hour, 161 g (2.37 mol) of imidazole in 0.7 l of THF are added dropwise in the course of 60 min. After a further 15 min, the mixture is filtered, the solid is washed with 0.5 l of THF, and the filtrate is concentrated to a volume of 1 l, filtered again, then completely concentrated, allowed to stand overnight at 0° C. under argon and again filtered through a frit.

Workup

  1. waitAfter a further 15 min
  2. filtrationthe mixture is filtered
  3. washthe solid is washed with 0.5 l of THF
  4. concentrationthe filtrate is concentrated to a volume of 1 l
  5. filtrationfiltered again
  6. concentrationcompletely concentrated
  7. waitto stand overnight at 0° C. under argon
  8. filtrationagain filtered through a frit

Sources & evidence

ORD record
ord-91d9bc8986d74d84bc2015f7055010af
Source dataset
uspto-grants-1998_07
Patent number
US05776964

Reaction notes

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