Sodium → HCID 135493231, compound

HRID 1392240Notes

Reaction equation

HRID 1392240 reaction equation
[OH:1][N:2]=[C:3](Cl)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10].[Na].[CH3:13][CH:14]1[CH2:19][C:18](=O)[CH2:17][C:16](=[O:21])[CH:15]1[C:22]([O:24][CH2:25][CH3:26])=[O:23]>C(O)C.O>[OH:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]1[C:17]2[C:16](=[O:21])[CH:15]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:14]([CH3:13])[CH2:19][C:18]=2[O:1][N:2]=1

Participants

6

Reactant 3

HCID 5360545SodiumHCID 11148304HCID 11148304, compoundHCID 136227647HCID 136227647, compound

Product 1

HCID 135493231HCID 135493231, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

N,2-Dihydroxybenzenecarboximidoyl chloride in 100 mL of ethanol was added to sodium salt of ethyl 2-methyl4,6-dioxocyclohexanecarboxylate in a solvent mixture of 125 mL of water and 75 mL of ethanol at a temperature of 55° C. over an hour. The reaction mixture was maintained at this temperature for 4 hours and then cooled down to room temperature. After diluting with water (100 mL), the mixture was extracted with ethyl acetate (2×100 mL). The resulting extract was washed with saturated sodium chloride aqueous solution (150 mL), dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was treated with diethyl ether to give the product (2.48 g) as white powders. The residue was further purified by silica gel preparative thin layer chromatography to give additional 2.15 g of the product as white powders (total amount yielded at the 2 steps: 4.63 g, yield: 60%). The physicochemical properties of the compound obtained are shown below.

Workup

  1. temperatureThe reaction mixture was maintained at this temperature for 4 hours
  2. extractionthe mixture was extracted with ethyl acetate (2×100 mL)
  3. extractionThe resulting extract
  4. washwas washed with saturated sodium chloride aqueous solution (150 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionThe residue was treated with diethyl ether

Sources & evidence

ORD record
ord-6ae112e39e7b4d318499b9a2dfc4c311
Source dataset
uspto-grants-2008_03
Patent number
US07342036B2

Reaction notes

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