Acetic Acid → Flumioxazin

HRID 1030963Notes

Reaction equation

HRID 1030963 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-3,4-dihydro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine (0.31 g), 3,4,5,6-tetrahydrophthalic anhydride (0.28 g) and acetic acid (3 ml) is heated under reflux for 2 hours. After being allowed to cool, water is added to the mixture, which is then extracted with ethyl acetate. The organic layer is washed with water, neutralized with sodium bicarbonate solution, dried and concentrated. The residue is purified by silica gel thin layer chromatography using a (1:2) mixture of ethyl acetate and hexane as the eluent to give the title product.

Workup

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

Sources & evidence

ORD record
ord-9ca94f23954940b287d7fec1c04cdf18
Source dataset
uspto-grants-1992_04
Patent number
US05108488

Reaction notes

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