Phosgene → 6-Methoxy-7-nitro-2H-3,1-benzoxazine-2,4(1H)-dione

HRID 855795Notes

Reaction equation

HRID 855795 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([O:14][CH3:15])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:16](Cl)(Cl)=[O:17]>C(Cl)(Cl)Cl.O1CCCC1>[CH3:15][O:14][C:8]1[C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:2]2[NH:1][C:16](=[O:17])[O:5][C:4](=[O:6])[C:3]=2[CH:7]=1

Participants

5

Reactant 2

HCID 6371Phosgene2×HCID 212602732-Amino-4-nitro-5-methoxybenzoic Acid

Product 1

HCID 713780046-Methoxy-7-nitro-2H-3,1-benzoxazine-2,4(1H)-dioneYield 100%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

2.0 g (9.4 mmol) of 2-amino-5-methoxy-4-nitrobenzoic acid were dissolved in 20 ml of chloroform and 10 ml of tetrahydrofuran, and 20 ml of 20% strength phosgene solution (1.8 M in toluene) were added. After 3 hours under reflux, a further 10 ml of phosgene solution were added at 60° C., and the mixture was stirred at 60° C. for a further 12 hours. The phosgene was distilled off and the residue was concentrated in vacuo after addition of toluene several times. 2.2 g (100%) of the desired product were obtained.

Workup

  1. temperatureAfter 3 hours under reflux
  2. distillationThe phosgene was distilled off
  3. concentrationthe residue was concentrated in vacuo
  4. additionafter addition of toluene several times

Sources & evidence

ORD record
ord-ccf77a2517c94ee481d1e439399bfdcb
Source dataset
uspto-grants-2007_08
Patent number
US07262220B2

Reaction notes

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