Diphosgene → HCID 14099380, compound

HRID 569694Notes

Reaction equation

HRID 569694 reaction equation
[NH2:1][C:2]1[C:3]([F:16])=[CH:4][C:5]2[O:10][CH2:9][C:8](=[O:11])[N:7]([CH2:12][CH2:13][CH3:14])[C:6]=2[CH:15]=1.Cl[C:18]([O:21]C(Cl)=O)(Cl)Cl.[N-]=C=O>C1(C)C=CC=CC=1>[F:16][C:3]1[C:2]([N:1]=[C:18]=[O:21])=[CH:15][C:6]2[N:7]([CH2:12][CH2:13][CH3:14])[C:8](=[O:11])[CH2:9][O:10][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 10426DiphosgeneHCID 105034IsocyanateHCID 14099379HCID 14099379, compound

Product 1

HCID 14099380HCID 14099380, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a stirred solution of 3.9 grams (0.017 mole) of 6-amino-7-fluoro-4-propyl-2H-1,4-benzoxazin-3(4H)-one in 240 ml of toluene was added a solution of 2.06 grams (0.0104 mole) of trichloromethylchloroformate in 10 ml of toluene. This mixture was stirred at room temperature for 1.5 hours and then was heated at reflux for approximately 18 hours. The mixture was cooled, and the solvent was removed by distillation at atmospheric pressure leaving a residue. This residue was subjected to reduced pressure for two hours to yield 4.36 grams of 7-fluoro-4-propyl-2H-1,4-benzoxazin-3(4H)-one-6 yl is isocyanate as a brown solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for approximately 18 hours
  3. temperatureThe mixture was cooled
  4. customthe solvent was removed by distillation at atmospheric pressure
  5. customleaving a residue
  6. waitThis residue was subjected to reduced pressure for two hours
  7. customto yield 4.36 grams of 7-fluoro-4-propyl-2H-1,4-benzoxazin-3(4H)-one-6 yl

Sources & evidence

ORD record
ord-a43c352e7af647acb08c73d2b4aeea30
Source dataset
uspto-grants-1988_03
Patent number
US04734124

Reaction notes

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