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

HRID 351854

Reaction equation

HRID 351854 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]([O:16]C(=O)OC(Cl)(Cl)Cl)(Cl)Cl>O1CCOCC1>[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:13](=[O:16])[O:8][C:7](=[O:9])[C:6]=2[CH:10]=1

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 1645925-Hydroxyanthranilic acid

Product 1

HCID 27593156-hydroxy-2,4-dihydro-1H-3,1-benzoxazine-2,4-dioneYield 281.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5-Hydroxyanthranilic acid (9.5 g, 62 mmol) was suspended in dioxane (50 mL), bis(trichloromethyl)carbonate (6 g, 20 mmol) was added (slightly exothermic), the suspension was refluxed for 1 h, allowed to cool to rt, the solid was filtered off and washed with dioxane, affording brown crystals (10.1 g, 90%), mp. 236° C. (dec).

Workup

  1. temperaturewas refluxed for 1 h
  2. filtrationthe solid was filtered off
  3. washwashed with dioxane

Sources & evidence

ORD record
ord-71eb5224684c469d86421c5cdea9da4e
Source dataset
uspto-grants-2004_06
Patent number
US06743789B2

Linked notes

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