Ethanol → HCID 70253628, compound

HRID 377562Notes

Reaction equation

HRID 377562 reaction equation
O.[NH2:2][NH2:3].[Cl:4][C:5]1[CH:6]=[C:7]([NH:12][C:13](=[O:32])[C:14]([N:17]2[C:22](=[O:23])[C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[C:20](C=O)OC2)([CH3:16])[CH3:15])[CH:8]=[C:9]([Cl:11])[CH:10]=1.[CH2:33]([OH:35])[CH3:34]>>[Cl:11][C:9]1[CH:8]=[C:7]([NH:12][C:13](=[O:32])[C:14]([N:17]2[C:22](=[O:23])[CH:21]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:20](=[N:2][NH2:3])[O:35][C:33]2=[CH2:34])([CH3:15])[CH3:16])[CH:6]=[C:5]([Cl:4])[CH:10]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 19354584HCID 19354584, compound

Product 1

HCID 70253628HCID 70253628, compound

Procedure

Hydrazine hydrate (0.06 ml) was added to a stirred solution of N-(3,5-dichlorophenyl)-2-(2,3-dihydro-6-formyl-4-oxo-5-phenyl-4H-1,3-oxazine-3-yl)-2-methylpropanamide (0.5 g) in ethanol at room temperature. After 0.5 hours the solvent was evaporated, the residue dissolved in ethyl acetate and washed with water and brine, 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-aminoiminomethylene-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide (compound 119, 0.19 g) as a pale yellow solid, m.p. 153-155° C.

Workup

  1. customAfter 0.5 hours the solvent was evaporated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried (magnesium sulphate)
  5. customevaporated
  6. customThe residue was purified
  7. customby dry column chromatography on silica gel
  8. washeluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-1f2c8f0eadeb47f8a4daad51da9c5233
Source dataset
uspto-grants-2000_02
Patent number
US06028032

Reaction notes

Loading…