Water → 5-(Morpholin-4-yl)isatoic anhydride

HRID 1985662Notes

Reaction equation

HRID 1985662 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].O.[O:18]=[C:19](Cl)OC(Cl)(Cl)Cl>O1CCOCC1>[N:11]1([C:8]2[CH:7]=[C:3]3[C:4]([O:6][C:19](=[O:18])[NH:1][C:2]3=[CH:10][CH:9]=2)=[O:5])[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 962WaterHCID 10426DiphosgeneHCID 70638872-Amino-5-(4-morpholinyl)benzoic acid

Product 1

HCID 866077765-(Morpholin-4-yl)isatoic anhydride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the mixture of 8.9 g of 2-amino-5-(morpholin-4-yl)benzoic 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, it is filtered off and washed with 30 mL of methanol. After drying 7 g of the title product is obtained, m.p.: 235° 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, it
  6. filtrationis filtered 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-4a9ef78629de47459fa0aaabb88b3307
Source dataset
uspto-grants-2009_06
Patent number
US07547696B2

Reaction notes

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