Methyl chloroformate → HCID 67410811, compound

HRID 1481523Notes

Reaction equation

HRID 1481523 reaction equation
[C:1]([C:5]1[N:6]=[CH:7][N:8]([CH3:10])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl[C:19]([O:21][CH3:22])=[O:20].CCOC(C)=O>C(#N)C>[CH3:22][O:21][C:19]([C:7]1[N:8]([CH3:10])[CH:9]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[N:6]=1)=[O:20]

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 22990479HCID 22990479, compound

Product 1

HCID 67410811HCID 67410811, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 4-tert-butyl-1-methyl-1H-imidazole (800 mg, 5.79 mmol, prepared as described in the previous step) and triethylamine (2.00 mL, 14.4 mmol) in acetonitrile (10 mL) at −30° C. was added methyl chloroformate (0.890 mL, 11.6 mmol) slowly under Ar. The resulting mixture was warmed to room temperature and continued to stir for 16 h. The resulting mixture was then treated with EtOAc (50 mL) and washed with H2O (2×20 mL), brine (20 mL) and then dried with Na2SO4. The solvent was evaporated in vacuo and the residue was purified by flash chromatography on silica gel (0:100-10:90 MeOH/DCM) to yield 4-tert-butyl-1-methyl-1H-imidazole-2-carboxylic acid methyl ester as a colorless oil. 1H-NMR (400 MHz, CDCl3) δ: 6.78 (s, 1H), 3.95 (s, 3H), 3.92 (s, 3H), 1.30 (s, 9H). Mass Spectrum (LCMS, ESI pos.) Calculated For C10H16N2O2: 197.1 (M+H). Measured: 197.1.

Workup

  1. customprepared
  2. customat −30° C.
  3. washwashed with H2O (2×20 mL), brine (20 mL)
  4. dry with materialdried with Na2SO4
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by flash chromatography on silica gel (0:100-10:90 MeOH/DCM)

Sources & evidence

ORD record
ord-ae2cb31640254a4498cff011e7557dd5
Source dataset
uspto-grants-2016_08
Patent number
US09409915B2

Reaction notes

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