Benzoyl isocyanate → 2-Phenyloxazol-4(5H)-one

HRID 1621149Notes

Reaction equation

HRID 1621149 reaction equation
[C:1]([N:9]=[C:10]=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](=[CH:14][Si](C)(C)C)=[N-]>C(#N)C>[C:2]1([C:1]2[O:8][CH2:14][C:10](=[O:11])[N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 78210Benzoyl isocyanateHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 69174032-Phenyloxazol-4(5H)-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
2.5 °C

Procedure

To a solution of benzoyl isocyanate (2 g, 12.2 mmol) in acetonitrile (40 mL) was added rapidly (diazomethyl)trimethylsilane (2M solution in hexane, 7.34 mL, 14.7 mmol) at 0-5° C., whereby the temperature rose to 15° C. (bubbling). The mixture was stirred at 0-5° C. for 1 h. Following solvent evaporation, the product was obtained after purification by flash chromatography (using silica gel and an ethyl acetate/heptane gradient) as yellow solid (1.84 g with 90% purity, 10.3 mmol, 84.0%) which was used without further purification for the next step.

Workup

  1. customrose to 15° C.
  2. custom(bubbling)
  3. customFollowing solvent evaporation
  4. customthe product was obtained
  5. customafter purification by flash chromatography (
  6. customan ethyl acetate/heptane gradient) as yellow solid (1.84 g with 90% purity, 10.3 mmol, 84.0%) which was used without further purification for the next step

Sources & evidence

ORD record
ord-5505cfd79dff47f2a773ce1a917a5018
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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