3-Fluorophthalic anhydride → Isopropyl 3-[2-chloro-4-fluoro-5-(3-fluorophthalimido)phenyl]tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate

HRID 52433

Reaction equation

HRID 52433 reaction equation
[NH2:1][C:2]1[C:3]([F:26])=[CH:4][C:5]([Cl:25])=[C:6]([N:8]2[C:13](=[O:14])[N:12]([CH3:15])[C:11](=[O:16])[N:10]([CH2:17][C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])[C:9]2=[O:24])[CH:7]=1.[F:27][C:28]1[CH:38]=[CH:37][CH:36]=[C:30]2[C:31]([O:33][C:34](=O)[C:29]=12)=[O:32]>C(O)(=O)C>[Cl:25][C:5]1[CH:4]=[C:3]([F:26])[C:2]([N:1]2[C:34](=[O:33])[C:29]3=[C:28]([F:27])[CH:38]=[CH:37][CH:36]=[C:30]3[C:31]2=[O:32])=[CH:7][C:6]=1[N:8]1[C:13](=[O:14])[N:12]([CH3:15])[C:11](=[O:16])[N:10]([CH2:17][C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])[C:9]1=[O:24]

Participants

4

Reactant 2

HCID 695513-Fluorophthalic anhydrideHCID 57313385isopropyl 3-(5-amino-2-chloro-4-fluorophenyl)tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate

Product 1

HCID 57181452Isopropyl 3-[2-chloro-4-fluoro-5-(3-fluorophthalimido)phenyl]tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of isopropyl 3-(5-amino-2-chloro-4-fluorophenyl)tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate (1.0 g, 2.6 mmol) and 3-fluorophthalic anhydride (0.51 g, 3.1 mmol) in acetic acid is refluxed for 6 hours, stirred at room temperature for several days and poured onto ice. The resultant aqueous mixture is filtered to obtain a solid. The solid is dried and chromatographed (silica gel/2.5% ether in methylene chloride solution) to give the title product as a yellow foam, mp 119°-125° C.

Workup

  1. additionpoured onto ice
  2. filtrationThe resultant aqueous mixture is filtered
  3. customto obtain a solid
  4. customThe solid is dried
  5. customchromatographed (silica gel/2.5% ether in methylene chloride solution)

Sources & evidence

ORD record
ord-f24bfe1cd6e5418f86c7bd6b933843d0
Source dataset
uspto-grants-1997_04
Patent number
US05616706

Linked notes

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