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

HRID 2176404Notes

Reaction equation

HRID 2176404 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-6e22afc3002f43a2bdddd4b617e81b32
Source dataset
uspto-grants-2015_06
Patent number
US09066519B2

Reaction notes

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