Ammonium Hydroxide → HCID 178492295, compound

HRID 705672Notes

Reaction equation

HRID 705672 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].[OH-].[NH4+:26]>C1COCC1.Cl[Hg]Cl>[NH2:26][C:12]([NH:11][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)=[C:13]1[C:18](=[O:19])[O:17][C:16]([CH3:21])([CH3:20])[O:15][C:14]1=[O:22]

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 578100945-[(3,4-Dimethoxy-phenylamino)-methylsulfanyl-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione

Product 1

HCID 178492295HCID 178492295, compoundYield 97%

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 (1.0 g, 2.8 mmol), 30% ammonium hydroxide (8.5 mL), HgCl2 (0.75 g, 2.8 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-[amino-(3,4-dimethoxy-phenylamino)-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione as a white solid (0.90 g, 97% yield) and this compound was used without further purification. LCMS: m/z 321 (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-2c364d3c41254de2a7328da92836da17
Source dataset
uspto-grants-2015_11
Patent number
US09174947B2

Reaction notes

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