Diphosgene → 2H-3,1-Benzoxazine-2,4(1H)-dione, 6-nitro-

HRID 655712

Reaction equation

HRID 655712 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[O:14]=[C:15](Cl)OC(Cl)(Cl)Cl>O1CCOCC1>[N+:11]([C:8]1[CH:7]=[C:3]2[C:4]([O:6][C:15](=[O:14])[NH:1][C:2]2=[CH:10][CH:9]=1)=[O:5])([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 120322-Amino-5-nitrobenzoic acid

Product 1

HCID 208212H-3,1-Benzoxazine-2,4(1H)-dione, 6-nitro-

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the mixture of 37 g of 2-amino-5-nitrobenzoic acid in 500 mL of dioxane, under stirring 24.5 mL of diphosgene was added dropwise. The mixture was heated under reflux conditions for 6 hours then it was evaporated to dryness. The residue was suspended in 100 mL of diethyl ether and filtered off to give 41.4 g of the title product as HCl salt, m.p.: 256-259° C. LC-MS: MH+ 209; Ret. time: 5 minutes.

Workup

  1. additionwas added dropwise
  2. temperatureThe mixture was heated under reflux conditions for 6 hours
  3. customit was evaporated to dryness
  4. filtrationfiltered off

Sources & evidence

ORD record
ord-057aa17fda5d414494afbf4e55888408
Source dataset
uspto-grants-2011_12
Patent number
US08071601B2

Linked notes

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