HCID 54511613, compound → HCID 19819238, compound

HRID 1030964Notes

Reaction equation

HRID 1030964 reaction equation
CS(O[CH2:6][C:7]([O:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1[N+:17]([O-])=O)=[O:8])(=O)=O>[Fe].C(O)(=O)C>[F:16][C:14]1[CH:13]=[CH:12][C:11]2[NH:17][CH2:6][C:7](=[O:8])[O:9][C:10]=2[CH:15]=1

Participants

4

Reactant 1

HCID 54511613HCID 54511613, compound

Product 1

HCID 19819238HCID 19819238, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

50 g (0.17 mol) of 5-fluoro-2-nitro-phenyl methylsulphonyloxyacetate are added in portions at 60° C. to a suspension of 5 g (0.89 mol) of iron powder in 450 ml of 5 per cent strength aqueous acetic acid. During this process, the temperature of the suspension rises to 90° C. The mixture is stirred for another 30 minutes at 90° C. and, after cooling, the undissolved components are filtered off. The filtration residue is suspended repeatedly in warm methanol and the suspension is filtered. After concentration, the combined methanol filtrates give 21.3 g (75% of theory) of 7-fluoro-3H-1,4-benzoxazin-2(4H)-one having a melting point of 199° C.

Workup

  1. customrises to 90° C
  2. temperatureafter cooling
  3. filtrationthe undissolved components are filtered off
  4. filtrationthe suspension is filtered
  5. concentrationAfter concentration

Sources & evidence

ORD record
ord-21bee78c5eee475690d47f1fa623f7c9
Source dataset
uspto-grants-1992_04
Patent number
US05108483

Reaction notes

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