Dimethadione → 2-[3-(1-Adamantyl)-2-(5,5-dimethyl-2,4-dioxooxazolidinyl)-3-oxopropanamido]-4-nitroanisole

HRID 1637152Notes

Reaction equation

HRID 1637152 reaction equation
[C:1]12([C:11](=[O:28])[CH:12](Cl)[C:13]([NH:15][C:16]3[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=3[O:25][CH3:26])=[O:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:29][C:30]1([CH3:37])[O:34][C:33](=[O:35])[NH:32][C:31]1=[O:36].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(OCC)(=O)C>[C:1]12([C:11](=[O:28])[CH:12]([N:32]3[C:31](=[O:36])[C:30]([CH3:37])([CH3:29])[O:34][C:33]3=[O:35])[C:13]([NH:15][C:16]3[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=3[O:25][CH3:26])=[O:14])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

6

Reactant 3

HCID 3081DimethadioneHCID 11430Potassium CarbonateHCID 193477582-[3-(1-Adamantyl)-2-chloro-3-oxopropanamido]-4-nitroanisole

Product 1

HCID 538796662-[3-(1-Adamantyl)-2-(5,5-dimethyl-2,4-dioxooxazolidinyl)-3-oxopropanamido]-4-nitroanisoleYield 79.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 16.28 g (0.04 mol) of [4], 5.17 g (0.04 mol) of 5,5-dimethyloxazolidine-2,4-dione, and 16.58 g (0.12) mol of anhydrous potassium carbonate in 380 mL of dried acetone was refluxed for 3 hours. Thin layer chromatographic analysis indicated that the reaction was complete. The reaction mixture was concentrated in vacuo to yield an orange-colored solid. It was dissolved in ethyl acetate and the organic layer was washed with HCl (10%) and brine until neutrality. The organic layer was dried, filtered, and concentrated to yield an oil which solidified upon standing. It was triturated in ligroin. The final dried product (15.92 g, 79.8%) gave one spot on TLC. All analytical data confirmed the assigned structure.

Workup

  1. temperaturewas refluxed for 3 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto yield an orange-colored solid
  4. washthe organic layer was washed with HCl (10%) and brine until neutrality
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield an oil which
  9. customIt was triturated in ligroin

Sources & evidence

ORD record
ord-8147e9c6089444d39b250676fc062f57
Source dataset
uspto-grants-2000_03
Patent number
US06040126

Reaction notes

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