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

HRID 403161Notes

Reaction equation

HRID 403161 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. The mixture was concentrated and chased with toluene and used as such in the next step.

Workup

  1. temperatureat reflux
  2. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-f455a7a783684f0cac8aa48d50ff3c70
Source dataset
uspto-grants-2014_06
Patent number
US08748348B2

Reaction notes

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