Isopropanol → Isopropyl 1H-imidazole-1-carboxylate

HRID 77430Notes

Reaction equation

HRID 77430 reaction equation
C1N=CN([C:6]([N:8]2[CH:12]=[N:11][CH:10]=[CH:9]2)=[O:7])C=1.[CH:13]([OH:16])([CH3:15])[CH3:14]>C(Cl)Cl>[CH:13]([O:16][C:6]([N:8]1[CH:9]=[CH:10][N:11]=[CH:12]1)=[O:7])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 3776IsopropanolHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 537559Isopropyl 1H-imidazole-1-carboxylateYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of CDI (2 g, 12.33 mmol), in DCM (25 mL) was added isopropyl alcohol (0.95 mL, 12.33 mmol) at 0° C. The reaction mixture was stirred at r.t. and progress of the reaction was monitored by TLC. On completion, the reaction mixture was diluted with DCM (100 mL). The organic layer was washed with water (25 mL), brine (25 mL), dried over anhydrous sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 1:10 ethyl acetate:Pet. ether) to provide title compound (330 mg, 77%) as colourless viscous oil.

Workup

  1. washThe organic layer was washed with water (25 mL), brine (25 mL)
  2. dry with materialdried over anhydrous sodium sulphate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography (silica gel, 1:10 ethyl acetate:Pet. ether)

Sources & evidence

ORD record
ord-a5bb1149895e4eb28456cd216de3f79e
Source dataset
uspto-grants-2014_09
Patent number
US08841306B2

Reaction notes

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