Phosgene → 2H-3,1-Benzoxazine-2,4(1H)-dione, 5-nitro-

HRID 1995508Notes

Reaction equation

HRID 1995508 reaction equation
Cl.[NH2:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:4]=1[C:5]([OH:7])=[O:6].[C:15](Cl)(Cl)=[O:16]>O.O1CCCC1>[N+:12]([C:8]1[CH:9]=[CH:10][CH:11]=[C:3]2[NH:2][C:15](=[O:16])[O:7][C:5](=[O:6])[C:4]=12)([O-:14])=[O:13]

Participants

5

Reactant 2

HCID 6371Phosgene2×HCID 70531720HCID 70531720, compound

Product 1

HCID 1347952H-3,1-Benzoxazine-2,4(1H)-dione, 5-nitro-

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 56.5 g of 2-amino-6-nitrobenzoic acid hydrochloride in 200 ml of demineralized water and 200 ml of tetrahydrofuran is cooled to 10° while stirring and treated with phosgene at 10°-30° for 1 hour, a precipitate resulting. The mixture is subsequently diluted with 300 ml of demineralized water and air is conducted through the suspension vigorously for about 3 hours (until the sample is negative for phosgene). The precipitate is filtered off, washed with water and dried in vacuo over phosphorus pentoxide. There is obtained 6-nitroisatoic acid anhydride as beige crystals of m.p. 220°-222° (decomposition).

Workup

  1. customa precipitate resulting
  2. filtrationThe precipitate is filtered off
  3. washwashed with water
  4. dry with materialdried in vacuo over phosphorus pentoxide

Sources & evidence

ORD record
ord-9bad052971e741c5b9c807e6c9221f3c
Source dataset
uspto-grants-1983_09
Patent number
US04405516

Reaction notes

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