Water → 6-hydroxy-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

HRID 362914

Reaction equation

HRID 362914 reaction equation
[OH:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([NH2:11])=[CH:4][CH:3]=1.Cl[C:13](Cl)([O:15]C(=O)OC(Cl)(Cl)Cl)Cl.O>O1CCOCC1>[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:13](=[O:15])[O:8][C:7](=[O:9])[C:6]=2[CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 94429TriphosgeneHCID 1645925-Hydroxyanthranilic acid

Product 1

HCID 27593156-hydroxy-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Step 1): A solution of 5-hydroxyanthranilic acid (500 mg, 3.26 mmol) and triphosgene (1.45 g, 4.9 mmol) in 1,4-dioxane (20 ml) was refluxed overnight. The reaction mixture was poured into H2O (30 ml), and then the precipitates were filtered and dried to give 6-hydroxy-1,2-dihydro-4H-3,1-benzoxazin-2,4-dione, 360 mg (62%).

Workup

  1. filtrationthe precipitates were filtered
  2. customdried

Sources & evidence

ORD record
ord-fe1e68e10f3b49f18152a75e8881998b
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Linked notes

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