Benzoic acid, 2-amino-5-iodo- → 6-iodo-2H-3,1-benzoxazine-2,4(1H)-dione
Reaction equation
[I:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([NH2:11])=[CH:4][CH:3]=1.[C:12](=O)(OC(Cl)(Cl)Cl)[O:13]C(Cl)(Cl)Cl>C1COCC1>[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
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
10 g (0.038 mol) of 5-iodoanthranilic acid were dissolved in 180 ml of THF, and 3.76 g (0.0127 mol) of bis(trichloromethyl) carbonate dissolved in 20 ml of THF were added. The mixture was then stirred at room temperature for 1 h and at 50° C. for 2 h. After cooling, the precipitate was filtered off with suction and dried. 7.8 g (71%) of 5-iodoisatoic anhydride were obtained as white crystals.
Workup
- additionwere added
- temperatureAfter cooling
- filtrationthe precipitate was filtered off with suction
- customdried
Sources & evidence
- ORD record
- ord-e013c49352ad4b38ab306c601d7622d6
- Source dataset
- uspto-grants-1997_12
- Patent number
- US05693637
Reaction notes
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