Acetonitrile → HCID 19979479, compound

HRID 1199616Notes

Reaction equation

HRID 1199616 reaction equation
Cl[CH2:2][C:3]1[CH:7]=[CH:6][O:5][N:4]=1.[F:8][C:9]1[C:19]([N:20]2[C:28](=[O:29])[C:27]3[CH2:26][CH2:25][CH2:24][CH2:23][C:22]=3[C:21]2=[O:30])=[CH:18][C:12]2[NH:13][C:14](=[O:17])[CH2:15][O:16][C:11]=2[CH:10]=1.C(#N)C.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[F:8][C:9]1[C:19]([N:20]2[C:28](=[O:29])[C:27]3[CH2:26][CH2:25][CH2:24][CH2:23][C:22]=3[C:21]2=[O:30])=[CH:18][C:12]2[N:13]([CH2:2][C:3]3[CH:7]=[CH:6][O:5][N:4]=3)[C:14](=[O:17])[CH2:15][O:16][C:11]=2[CH:10]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 49130253-(Chloromethyl)-1,2-oxazoleHCID 137721852-(7-Fluoro-3-oxo-4H-1,4-benzoxazin-6-yl)-4,5,6,7-tetrahydroisoindole-1,3-dione

Product 1

HCID 19979479HCID 19979479, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A compound of 3-(chloromethyl)-isoxazole (1.2 g) was added dropwise at a temperature of 20° to 30° C. under stirring to a mixture of 7-fluoro-6-(4,5,6,7-tetrahydro-2H-isoindole-1,3-dion-2-yl)-2H-1,4-benzoxazin-3(4H)-one (3.16 g), acetonitrile (50 ml) and potassium carbonate (1.5 g). The reaction mixture was heated under refluxing for 3 hours, cooled to room temperature, and filtered. The filtrate was concentrated under a reduced pressure to dryness. The resultant residue was mixed with toluene (150 ml) to form a suspension, which was then filtered to remove the undissolved materials therefrom. The filtrate was concentrated under a reduced pressure so as to obtain a viscous material, which was thereafter dissolved in a minimum amount of ethanol. The ethanol solution was cooled to precipitate a crystalline product. This product was separated by filtration and dried, so that the aimed compound, i.e. 7-fluoro-4-(isoxazol-3-ylmethyl)-6-(4,5,6,7-tetrahydro-2H-isoindole-1,3-dion-2-yl)-2H-1,4-benzoxazin-3(4H)-one (3.3 g) was obtained. m.p. 206°-210° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder refluxing for 3 hours
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under a reduced pressure to dryness
  5. additionThe resultant residue was mixed with toluene (150 ml)
  6. customto form a suspension, which
  7. filtrationwas then filtered
  8. customto remove the undissolved materials
  9. concentrationThe filtrate was concentrated under a reduced pressure so as
  10. customto obtain a viscous material, which
  11. customto precipitate a crystalline product
  12. customThis product was separated by filtration
  13. dry with materialdried, so that the aimed compound

Sources & evidence

ORD record
ord-59e4178ff31d4f7f98fb23a38521790e
Source dataset
uspto-grants-1990_02
Patent number
US04902335

Reaction notes

Loading…