Water → HCID 54409863, compound

HRID 1709362Notes

Reaction equation

HRID 1709362 reaction equation
[C:1]([O:7][CH2:8][CH2:9][S:10][C:11](=[O:13])[CH3:12])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[N+:14]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=O)([O-:16])=[O:15].C([O-])(=O)C.[NH2+]1CCCCC1.O>C1C=CC=CC=1>[N+:14]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=[C:2]([C:3]([CH3:5])=[O:4])[C:1]([O:7][CH2:8][CH2:9][S:10][C:11](=[O:13])[CH3:12])=[O:6])([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 74493-NitrobenzaldehydeHCID 3014295Piperidinium acetateHCID 10081624HCID 10081624, compound

Product 1

HCID 54409863HCID 54409863, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 7.0 g of 2-acetylthioethyl acetoacetate, 5.14 g of 3-nitrobenzaldehyde and 0.99 g of piperidinium acetate in 100 ml of benzene was heated at reflux under azeotropic dehydration conditions for 2 hours. The reaction mixture was poured into water and extracted with benzene, and the extract was washed with water and dried over anhydrous sodium sulfate. Evaporation of the solvent under reduced pressure gave 9.83 g of 2-acetylthioethyl 2-(3-nitrobenzilidene)acetoacetate.

Workup

  1. temperatureat reflux under azeotropic dehydration conditions for 2 hours
  2. extractionextracted with benzene
  3. washthe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-860782246f514acf991286a26f706177
Source dataset
uspto-grants-1990_08
Patent number
US04948899

Reaction notes

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