Diphosgene → 2,2,7-trifluoro-6-isocyanato-4-(prop-2-ynyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 1404898Notes

Reaction equation

HRID 1404898 reaction equation
[NH2:1][C:2]1[C:17]([F:18])=[CH:16][C:5]2[O:6][C:7]([F:15])([F:14])[C:8](=[O:13])[N:9]([CH2:10][C:11]#[CH:12])[C:4]=2[CH:3]=1.[O:19]=[C:20](Cl)OC(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[F:15][C:7]1([F:14])[O:6][C:5]2[CH:16]=[C:17]([F:18])[C:2]([N:1]=[C:20]=[O:19])=[CH:3][C:4]=2[N:9]([CH2:10][C:11]#[CH:12])[C:8]1=[O:13]

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 866695376-amino-2,2,7-trifluoro-4-(prop-2-ynyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

Product 1

HCID 866643002,2,7-trifluoro-6-isocyanato-4-(prop-2-ynyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To 6-amino-2,2,7-trifluoro-4-(prop-2-ynyl)-2H-benzo[b][1,4]oxazin-3(4H)-one (5.1 g, 19.91 mmol) in dry toluene was dropwise added diphosgene (2.64 ml, 21.90 mmol) in dry toluene. The resulting mixture was stirred overnight at reflux. Concentrated and chased with toluene and used as such in the next step.

Workup

  1. temperatureat reflux
  2. concentrationConcentrated

Sources & evidence

ORD record
ord-90520183cd774f5b989211512cb72e3f
Source dataset
uspto-grants-2014_12
Patent number
US08916501B2

Reaction notes

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