Acetic Anhydride → HCID 86755151, compound

HRID 377561Notes

Reaction equation

HRID 377561 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[Cl:8][C:9]1[CH:10]=[C:11]([NH:16][C:17](=[O:37])[C:18]([N:21]2[C:26](=[O:27])[CH:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:24](=[N:34][OH:35])[O:23][C:22]2=[CH2:36])([CH3:20])[CH3:19])[CH:12]=[C:13]([Cl:15])[CH:14]=1>N1C=CC=CC=1>[Cl:8][C:9]1[CH:10]=[C:11]([NH:16][C:17](=[O:37])[C:18]([N:21]2[C:26](=[O:27])[CH:25]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:24](=[N:34][O:35][C:1](=[O:3])[CH3:2])[O:23][C:22]2=[CH2:36])([CH3:20])[CH3:19])[CH:12]=[C:13]([Cl:15])[CH:14]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 86755150HCID 86755150, compound

Product 1

HCID 86755151HCID 86755151, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic 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-1,3-oxazin-3-yl)-2-methylpropanamide (0.4 g) in pyridine (3 ml) at -5° C. After 1.5 hours the mixture was poured into ice/water and extracted (ethyl acetate). The extract was washed with hydrochloric acid (2M) and with 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-acetoxyiminomethylene-2,3-dihydro-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide (compound 118, 0.32 g) as an off-white solid, m.p. 125-127° C.

Workup

  1. extractionextracted (ethyl acetate)
  2. washThe extract was washed with hydrochloric acid (2M) and with brine
  3. dry with materialdried (magnesium sulphate)
  4. customevaporated
  5. customThe residue was purified
  6. customby dry column chromatography on silica gel
  7. washeluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-36b6b9ff730f45f7909d381bf1194ee8
Source dataset
uspto-grants-2000_02
Patent number
US06028032

Reaction notes

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