Water → 6-iodo-2H-3,1-benzoxazine-2,4(1H)-dione

HRID 1655685Notes

Reaction equation

HRID 1655685 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[C:12](=O)([O-])[O-:13].[Na+].[Na+].O.C(Cl)(Cl)=O>C1(C)C=CC=CC=1>[I:1][C:2]1[CH:10]=[C:6]2[C:7]([O:9][C:12](=[O:13])[NH:11][C:5]2=[CH:4][CH:3]=1)=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6371PhosgeneHCID 10340Sodium CarbonateHCID 72911Benzoic acid, 2-amino-5-iodo-

Product 1

HCID 2944806-iodo-2H-3,1-benzoxazine-2,4(1H)-dioneYield 84.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mechanically stirred solution of 26.3 grams of 5-iodo-2-amino benzoic acid (0.1 mol), 10.6 grams of sodium carbonate (0.1 mol), and 250 mL water, cooled to 0° C., was slowly added, via an addition funnel, 80 mL of a 1.93M solution of phosgene in toluene. After 2 hours, the precipitated product was isolated by filtration. The solids were washed with 200 mL water, 300 mL of a 1:1 mixture ethanol and ether, 200 mL of ether, and dried under vacuum to yield 24.3 grams (84%) of 5-iodoisatoic anhydride (264°-268° C., decomposition).

Workup

  1. additionwas slowly added, via an addition funnel
  2. customthe precipitated product was isolated by filtration
  3. washThe solids were washed with 200 mL water, 300 mL of a 1:1 mixture ethanol and ether, 200 mL of ether
  4. customdried under vacuum

Sources & evidence

ORD record
ord-9fe94da23f524fc19a707438534b4fc5
Source dataset
uspto-grants-1993_10
Patent number
US05250679

Reaction notes

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