Phosgene → 5-iodo-N-methylisatoic anhydride

HRID 865352Notes

Reaction equation

HRID 865352 reaction equation
[I:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([NH:11][CH3:12])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:19](Cl)(Cl)=[O:20]>O>[I:1][C:2]1[CH:10]=[C:6]2[C:7]([O:9][C:19](=[O:20])[N:11]([CH3:12])[C:5]2=[CH:4][CH:3]=1)=[O:8]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 11430Potassium CarbonateHCID 222818675-Iodo-2-(methylamino)benzoic acid

Product 1

HCID 538260965-iodo-N-methylisatoic anhydrideYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mechanically stirred solution of 5-iodo-N-methylanthranilic acid (40 grams 0.144 mol), potassium carbonate (19.95 grams, 0.144 mol), and 500 ml water at 0° C. was added phosgene (1.93M solution in toluene, 0.2 mol, 104 mL) over a period of 1 hr. the resulting slurry was stirred for an additional 3 hrs and the solids isolated by filtration, washing with water, and a small amount (70 mL) of ether. The solids were dried overnight in vacuo to yield 34 grams (78%) of 5-iodo-N-methylisatoic anhydride. 1H NMR (DMSO-d6) 8.18 (1H, bs, C6-H), 8.08 (1H, bd, 3JHH =8 Hz, C4-H), 7.12 (1H, d, 3JHH =8 Hz, C3-H), 3.42 (3H, s, NCH3).

Workup

  1. customthe solids isolated by filtration
  2. washwashing with water
  3. customThe solids were dried overnight in vacuo

Sources & evidence

ORD record
ord-898fef99b24240629802d34b1fa1e1e2
Source dataset
uspto-grants-1996_10
Patent number
US05565449

Reaction notes

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