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

HRID 455869Notes

Reaction equation

HRID 455869 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12](SC)=[C:13]2[C:18](=[O:19])[O:17][C:16]([CH3:21])([CH3:20])[O:15][C:14]2=[O:22])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:25][NH2:26]>C1COCC1.Cl[Hg]Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]([NH:26][CH3:25])=[C:13]2[C:18](=[O:19])[O:17][C:16]([CH3:21])([CH3:20])[O:15][C:14]2=[O:22])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 578100945-[(3,4-Dimethoxy-phenylamino)-methylsulfanyl-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione

Product 1

HCID 578101695-[(3,4-Dimethoxy-phenylamino)-methylamino-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dioneYield 101.9%

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-[(3,4-dimethoxy-phenylamino)-methylsulfanyl-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione (0.50 g, 1.4 mmol), methylamine (2 M in THF, 0.75 mL. 1.5 mmol), HgCl2 (0.38 g, 1.4 mmol) in THF (5 mL) was stirred at room temperature for 30 minutes. The mixture was extracted with DCM and water (3×) and dried with Na2SO4. Concentration in vacuo afforded 5-[(3,4-dimethoxy-phenylamino)-methylamino-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione as a yellow solid (0.48 g, 99% yield) and this compound was used without further purification. LCMS: m/z 335 (M−H)−.

Workup

  1. extractionThe mixture was extracted with DCM and water (3×)
  2. dry with materialdried with Na2SO4
  3. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-d62f0011c825406db4e2ca804dd5f78b
Source dataset
uspto-grants-2013_07
Patent number
US08497284B2

Reaction notes

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