Phosgene → 7-isocyanato-4-methyl-2H-chromen-2-one

HRID 1916043Notes

Reaction equation

HRID 1916043 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:13])=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.[C:14](Cl)(Cl)=[O:15]>C1(C)C=CC=CC=1>[N:1]([C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:13])=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1)=[C:14]=[O:15]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 922497-Amino-4-methylcoumarin

Product 1

HCID 583781007-isocyanato-4-methyl-2H-chromen-2-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A round bottom flask was charged with 7-amino-4-methyl-coumarin (50 mg, 0.285 mmol) under argon and treated with a 20% phosgene in toluene solution (2 ml) under. The reaction mixture was heated at reflux for 15 hrs under argon during which time a white solid precipitated out of solution. After cooling, the excess phosgene was removed by bubbling argon gas through from the solution for 10 minutes. The reaction mixture was then evaporated to afford the product as white solid, which was used directly in the next step. Yield: 50 mg (87%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 15 hrs under argon during which time a white solid
  3. customprecipitated out of solution
  4. temperatureAfter cooling
  5. customthe excess phosgene was removed
  6. customby bubbling argon gas through from the solution for 10 minutes
  7. customThe reaction mixture was then evaporated

Sources & evidence

ORD record
ord-1ea8e4a90d66403db1059313f7f9be6e
Source dataset
uspto-grants-2013_12
Patent number
US08618096B2

Reaction notes

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