Water → 5-iodo-N-methylisatoic anhydride

HRID 908547Notes

Reaction equation

HRID 908547 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([NH:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].C(=O)([O-])[O-].[Na+].[Na+].O.[C:20](Cl)(Cl)=[O:21]>C1(C)C=CC=CC=1>[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:20](=[O:21])[O:9][C:7](=[O:8])[C:6]=2[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6371PhosgeneHCID 10340Sodium CarbonateHCID 222818675-Iodo-2-(methylamino)benzoic acid

Product 1

HCID 538260965-iodo-N-methylisatoic anhydride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 5-iodo-2-(methylamino)benzoic acid (10 g, 36 mmol), sodium carbonate (4 g, 36 mmol) and water (130 ml, 7218 mmol), cooled to 0° C., was slowly added, via addition funnel, a 2M phosgene (18 ml, 36 mmol) solution in toluene. After 2 hrs, the precipitated product was isolated by filtration. The solids were washed with 100 ml of water, 150 ml of a 1:1 mixture ethanol and ether, 100 ml of ether, and dried under vacuum to give the desired product. Yield=7.15 g.

Workup

  1. additionwas slowly added, via addition funnel
  2. customthe precipitated product was isolated by filtration
  3. washThe solids were washed with 100 ml of water, 150 ml of a 1:1 mixture ethanol and ether, 100 ml of ether
  4. customdried under vacuum

Sources & evidence

ORD record
ord-9f22148f88324b2ca25a0fd3adecc378
Source dataset
uspto-grants-2011_09
Patent number
US08017626B2

Reaction notes

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