Potassium Carbonate → 3-((2-Ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino)-2-hydroxy-N,N-dimethylbenzamide

HRID 1927575Notes

Reaction equation

HRID 1927575 reaction equation
[NH2:1][C:2]1[C:3]([OH:13])=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([N:7]([CH3:9])[CH3:8])=[O:6].[CH2:14]([O:16][C:17]1[C:18](=O)[C:19](=[O:24])[C:20]=1[O:21]CC)[CH3:15].C([O-])([O-])=O.[K+].[K+]>CCO.CO>[CH2:14]([O:16][C:17]1[C:20](=[O:21])[C:19](=[O:24])[C:18]=1[NH:1][C:2]1[C:3]([OH:13])=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([N:7]([CH3:9])[CH3:8])=[O:6])[CH3:15]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 123228Diethyl squarateHCID 160984833-Amino-2-hydroxy-N,N-dimethylbenzamide

Product 1

HCID 118554143-((2-Ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino)-2-hydroxy-N,N-dimethylbenzamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

44 g of 3-amino-2-hydroxy-N,N-dimethyl-benzamide are dissolved in 880 ml of EtOH. 46 g of 3,4-diethoxy-3-cyclobuten-1,2-dione and 4.4 g of K2CO3 are added and the reaction mixture obtained is stirred overnight at rt. Solvent is evaporated. A residue obtained is purified by column chromatography over 500 g of silica using CH2Cl2/MeOH 98/2 as eluent. The product-containing fractions are combined and solvent is evaporated. A residue obtained is suspended in 1 l of MeOH and filtered. This process is repeated a further 3 times. The title compound is obtained.

Workup

  1. customthe reaction mixture obtained
  2. customSolvent is evaporated
  3. customA residue obtained
  4. customis purified by column chromatography over 500 g of silica
  5. customsolvent is evaporated
  6. customA residue obtained
  7. filtrationfiltered

Sources & evidence

ORD record
ord-f32b5560f15c48baa7c7a723d17605f1
Source dataset
uspto-grants-2012_05
Patent number
US08183281B2

Reaction notes

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