Acetic Acid → Flumioxazin

HRID 1638826Notes

Reaction equation

HRID 1638826 reaction equation
[NH2:1][C:2]1[C:3]([F:16])=[CH:4][C:5]2[O:10][CH2:9][C:8](=[O:11])[N:7]([CH2:12][C:13]#[CH:14])[C:6]=2[CH:15]=1.[C:17]1(=O)[O:22][C:20](=[O:21])[C:19]2[CH2:23][CH2:24][CH2:25][CH2:26][C:18]1=2.C(O)(=O)C>O>[F:16][C:3]1[C:2]([N:1]2[C:20](=[O:21])[C:19]3[CH2:23][CH2:24][CH2:25][CH2:26][C:18]=3[C:17]2=[O:22])=[CH:15][C:6]2[N:7]([CH2:12][C:13]#[CH:14])[C:8](=[O:11])[CH2:9][O:10][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 111603236-amino-7-fluoro-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-3-one

Product 1

HCID 92425Flumioxazin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-amino-7-fluoro-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-one (0.31 g), 3,4,5,6-tetrahydrophthalic anhydride (0.28 g) and acetic acid (3 ml) was heated under reflux for 2 hours. After being allowed to cool, water was added to the mixture, which was then extracted with ethyl acetate. The organic layer was washed with water, neutralized with sodium bicarbonate solution, dried and concentrated. The residue was purified by silica gel thin layer chromatography using a mixture of ethyl acetate and hexane (1:2) as an eluent to give 2-[7-fluoro-4-(2-propynyl)-2H-1,4-benzoxazin-3(4H)-on-6-yl]-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (0.12 ). m.p., 196.0° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. temperatureto cool
  4. extractionwas then extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel thin layer chromatography
  9. additiona mixture of ethyl acetate and hexane (1:2) as an eluent

Sources & evidence

ORD record
ord-181b75e438be4aec94de0d50f5e36f3c
Source dataset
uspto-grants-1989_11
Patent number
US04880925

Reaction notes

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