Pyridine → HCID 19354655, compound

HRID 377563Notes

Reaction equation

HRID 377563 reaction equation
FC(F)(F)[C:3]([O:5][C:6](=O)[C:7](F)(F)F)=O.[Cl:14][C:15]1[CH:16]=[C:17]([NH:22][C:23](=[O:43])[C:24]([N:27]2[C:32](=[O:33])[CH:31]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)C(=NO)C(=C)O2)([CH3:26])[CH3:25])[CH:18]=[C:19]([Cl:21])[CH:20]=1.C(OCC)(=O)C.[N:50]1C=CC=CC=1>>[Cl:14][C:15]1[CH:16]=[C:17]([NH:22][C:23](=[O:43])[C:24]([N:27]2[C:32](=[O:33])[C:31]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[C:6]([C:7]#[N:50])[O:5][CH2:3]2)([CH3:25])[CH3:26])[CH:18]=[C:19]([Cl:21])[CH:20]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 9845Trifluoroacetic anhydrideHCID 86755152HCID 86755152, compound

Product 1

HCID 19354655HCID 19354655, compound

Procedure

Trifluoroacetic anhydride (3 ml) was added to a stirred solution of N-(3,5-dichlorophenyl)-2-(2,3-dihydro-6-hydroxyiminomethylene-4-oxo-5-phenyl-4H-2,3-oxazin-3-yl)-2-methylpropanamide (0.4 g) in pyridine (4 ml) at -5° C. After 0.5 hours ice and ethyl acetate was added and the mixture stirred for 1 hour. The organic phase was washed (water), dried (magnesium sulphate) and evaporated. The residue was purified by dry column chromatography on silica gel, eluting with hexane/ethyl acetate to give N-(3,5-dichlorophenyl)-2-(6-cyano-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide (compound 120, 0.16 g) as a white solid, m.p. 132.5-135° C.

Workup

  1. washThe organic phase was washed (water)
  2. dry with materialdried (magnesium sulphate)
  3. customevaporated
  4. customThe residue was purified
  5. customby dry column chromatography on silica gel
  6. washeluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-37fcc5a1291747b7b15189d2c0092e67
Source dataset
uspto-grants-2000_02
Patent number
US06028032

Reaction notes

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