2,2-Dimethyl-1,3-dioxane-4,6-dione → 5-[(2-Bromo-5-methoxy-phenylamino)-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione

HRID 1437359Notes

Reaction equation

HRID 1437359 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[NH2:10].[CH3:11][C:12]1([CH3:20])[O:17][C:16](=[O:18])[CH2:15][C:14](=[O:19])[O:13]1.[CH:21](OCC)(OCC)OCC>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[NH:10][CH:21]=[C:15]1[C:16](=[O:18])[O:17][C:12]([CH3:20])([CH3:11])[O:13][C:14]1=[O:19]

Participants

5

Reactant 3

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 31214Ethyl orthoformateHCID 7930162-Bromo-5-methoxyaniline

Product 1

HCID 686990625-[(2-Bromo-5-methoxy-phenylamino)-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dioneYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-bromo-5-methoxy-phenylamine (16.1 g, 80 mmol), 2,2-dimethyl-[1,3]dioxane-4,6-dione (Meldrum's acid) (13.7 g, 95 mmol) and triethyl orthoformate (14.1 g, 95 mmol) in ethanol (82 ml) was heated to reflux for 2 hours then allowed to cool to room temperature. Filtration and drying in vacuo afforded a white solid (25.7 g, 91%)

Workup

  1. temperatureto reflux for 2 hours
  2. filtrationFiltration
  3. customdrying in vacuo

Sources & evidence

ORD record
ord-93fe04187f30472582b9d69fcaac80e0
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

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