Water → 5-Dimethylaminoisatoic anhydride

HRID 655694Notes

Reaction equation

HRID 655694 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]([CH3:13])[CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].O.[O:15]=[C:16](Cl)OC(Cl)(Cl)Cl>O1CCOCC1>[CH3:12][N:11]([CH3:13])[C:8]1[CH:7]=[C:3]2[C:4]([O:6][C:16](=[O:15])[NH:1][C:2]2=[CH:10][CH:9]=1)=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 10426DiphosgeneHCID 127157942-Amino-5-(dimethylamino)benzoic acid

Product 1

HCID 127157955-Dimethylaminoisatoic anhydride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the mixture of 8.9 g of 2-amino-5-dimethylaminobenzoic acid in 60 mL of dioxane, under stirring and external cold water cooling 10 mL of diphosgene is added dropwise. The mixture is heated under reflux conditions for 4 hours. From the cold reaction mixture the solid material is filtered off, washed with 50 mL of ether. The product is stirred for 5 minutes in the mixture of 50 mL of methanol and 5 mL of triethylamine, filtered off, washed with 30 mL of methanol. After drying 7 g of the title product is obtained, m.p.: 258° C.

Workup

  1. temperatureThe mixture is heated under reflux conditions for 4 hours
  2. customFrom the cold reaction mixture the solid material
  3. filtrationis filtered off
  4. washwashed with 50 mL of ether
  5. stirringThe product is stirred for 5 minutes in the mixture of 50 mL of methanol and 5 mL of triethylamine
  6. filtrationfiltered off
  7. washwashed with 30 mL of methanol
  8. dry with materialAfter drying 7 g of the title product
  9. customis obtained

Sources & evidence

ORD record
ord-82d062da84ea46d4b612be3357f7e29d
Source dataset
uspto-grants-2011_12
Patent number
US08071601B2

Reaction notes

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