Benzoic acid, 2-amino-5-iodo- → 6-iodo-2H-3,1-benzoxazine-2,4(1H)-dione

HRID 1276619Notes

Reaction equation

HRID 1276619 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl[C:13](Cl)([O:15]C(=O)OC(Cl)(Cl)Cl)Cl>O1CCOCC1>[I:11][C:8]1[CH:9]=[CH:10][C:2]2[NH:1][C:13](=[O:15])[O:5][C:4](=[O:6])[C:3]=2[CH:7]=1

Participants

4

Reactant 2

HCID 72911Benzoic acid, 2-amino-5-iodo-HCID 94429Triphosgene

Product 1

HCID 2944806-iodo-2H-3,1-benzoxazine-2,4(1H)-dioneYield 102.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-amino-5-iodobenzoic acid (25 g, 95.05 mmol) and triphosgene (77.1 g, 260.4 mmol) in dioxane (316 mL) was heated to reflux for 8 h. The resulting solid was filtered and washed with diethyl ether to give 28.1 g of the title compound, 1H NMR (300 MHz, Me2SO-d6): δ6.96 (d,1H); 8.02 (dd,1H); 8.13 (d,1H); 11.82 (br s,1H); m/e 288 deprotonated parent molecular ion (m/e) measured by mass spectrometry using atmospheric pressure chemical ionization in the negative ion mode (APCI-).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 8 h
  3. filtrationThe resulting solid was filtered
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-9682833c55fe46a9b06b81af3c4202ba
Source dataset
uspto-grants-2000_12
Patent number
US06166208

Reaction notes

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