Potassium Hydroxide → 2-Amino-6-m-fluorophenyl-1,3-oxazine-4-one

HRID 1248034Notes

Reaction equation

HRID 1248034 reaction equation
S(O)(O)(=O)=O.C[NH:7][C:8](=[NH:10])S.[OH-].[K+].C([O:15][C:16](=O)[CH2:17][C:18](=[O:26])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=1)C.O1C=CC=CN1>O>[NH2:10][C:8]1[O:26][C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)=[CH:17][C:16](=[O:15])[N:7]=1

Participants

6

Reactant 4

HCID 14797Potassium HydroxideHCID 2063904Ethyl 3-(3-fluorophenyl)-3-oxopropanoateHCID 12313776OxazineHCID 178485225HCID 178485225, compound

Product 1

HCID 133709352-Amino-6-m-fluorophenyl-1,3-oxazine-4-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 16.6 g (0.597M) of methylthiopseudourea sulfate is added 66 ml of H2O+13.0 g of KOH. With vigorous stirring, 20 g (71.9 mM) of ethyl-m-fluorobenzoylacetate is added and the reaction mixture is allowed to stir, at ambient temperature, for 18 hours. The solids are filtered and washed well with H2O followed by diethylether. The crude title compound is dried at 60° C. in a vacuum over to yield 16.0 g (>100 percent). To 6.8 g of crude powdered oxazine is added 100 ml of H2O and heated to 70° C., cooled, filtered and washed solids. Yield of 2-amino-6-m-fluorophenyl-1,3-oxazine-4-one of 3.60 g (53 percent of rec. yield).

Workup

  1. filtrationThe solids are filtered
  2. washwashed well with H2O
  3. dry with materialThe crude title compound is dried at 60° C. in a vacuum over
  4. customto yield 16.0 g (>100 percent)
  5. temperatureheated to 70° C.
  6. temperaturecooled
  7. filtrationfiltered
  8. washwashed solids

Sources & evidence

ORD record
ord-38b422e04f6949bb84db4aad1c577c29
Source dataset
uspto-grants-1985_06
Patent number
US04521599

Reaction notes

Loading…