3,4-Dimethoxyaniline → 5-[(3,4-Dimethoxy-phenylamino)-methylsulfanyl-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione

HRID 705670Notes

Reaction equation

HRID 705670 reaction equation
CS[C:3]([S:14][CH3:15])=[C:4]1[C:9](=[O:10])[O:8][C:7]([CH3:12])([CH3:11])[O:6][C:5]1=[O:13].[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[NH2:21]>CCO>[CH3:16][O:17][C:18]1[CH:19]=[C:20]([NH:21][C:3]([S:14][CH3:15])=[C:4]2[C:9](=[O:10])[O:8][C:7]([CH3:12])([CH3:11])[O:6][C:5]2=[O:13])[CH:22]=[CH:23][C:24]=1[O:25][CH3:26]

Participants

4

Reactant 2

HCID 227703,4-DimethoxyanilineHCID 17451285-[Bis(methylsulfanyl)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 578100945-[(3,4-Dimethoxy-phenylamino)-methylsulfanyl-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dioneYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Commercially available 5-(bis-methylsulfanyl-methylene)-2,2-dimethyl-[1,3]dioxane-4,6-dione (3.5 g, 14 mmol) and 3,4-dimethoxyaniline (2.2 g, 14 mmol) were reflux in EtOH (20 mL) for 2 hours. The EtOH was removed under reduced pressure and EtOAc was added to the residue. The product was filtered and washed with cold EtOAc (3×). 5-[(3,4-dimethoxy-phenylamino)-methylsulfanyl-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione was obtained as a white solid (1.7 g, 47% yield) and used without further purification. LCMS: m/z 352 (M−H)−.

Workup

  1. customThe EtOH was removed under reduced pressure and EtOAc
  2. additionwas added to the residue
  3. filtrationThe product was filtered
  4. washwashed with cold EtOAc (3×)

Sources & evidence

ORD record
ord-ee9a82b5cfd04d2e9220399b9f58d35d
Source dataset
uspto-grants-2015_11
Patent number
US09174947B2

Reaction notes

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