Thionyl Chloride → 3-Chloroisatoic anhydride

HRID 838992

Reaction equation

HRID 838992 reaction equation
C([O:3][C:4]([NH:6][C:7]1[C:8](=[CH:12][CH:13]=[CH:14][C:15]=1[Cl:16])[C:9]([OH:11])=[O:10])=O)C.S(Cl)(Cl)=O>O1CCOCC1>[Cl:16][C:15]1[C:7]2[NH:6][C:4](=[O:3])[O:10][C:9](=[O:11])[C:8]=2[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 203255893-Chloro-2-[(ethoxycarbonyl)amino]benzoic acid

Product 1

HCID 5175353-Chloroisatoic anhydride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

468 gm of N-ethoxycarbonyl-3-chloro-anthranilic acid (m.p. 111°-114° C) were refluxed in 1500 ml of dioxane with 420 ml of thionyl chloride for 3 hours while stirring. Thereafter, the reaction solution was evaporated in vacuo until crystallization started, and then cooled. The precipitate was collected by suction filtration and washed with ether. 8-Chloro-2H-3,1-benzoxazine-2,4(1H)-dione, m.p. 225°-230° C, was obtained.

Workup

  1. customThereafter, the reaction solution was evaporated in vacuo until crystallization
  2. temperaturecooled
  3. filtrationThe precipitate was collected by suction filtration
  4. washwashed with ether

Sources & evidence

ORD record
ord-eabb9a499dfa4e3fa44b3f4e83befdd6
Source dataset
uspto-grants-1978_06
Patent number
US04093734

Linked notes

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