Citric Acid → HCID 58355436, compound

HRID 1509616Notes

Reaction equation

HRID 1509616 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=S)[C:9]([O:11][CH2:12][CH3:13])=[O:10].[C:15]([NH:23][NH2:24])(=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:25](O)(=O)[CH2:26]C(CC(O)=O)(C(O)=O)O>C(O)CCC>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:23][N:24]=[C:8]1[C:9]([O:11][CH2:12][CH2:13][CH2:25][CH3:26])=[O:10]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 11955BenzoylhydrazineHCID 59356644HCID 59356644, compound

Product 1

HCID 58355436HCID 58355436, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
140 °C

Procedure

Ethyl [(4-methoxybutyl)amino](thioxo)acetate (1.2 g) and benzohydrazide (745 mg) were dissolved in 1-butanol (10 ml), and the mixture was stirred at 140° C. for 15 hr. The reaction mixture was cooled to room temperature, 10% aqueous citric acid solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (8:2) was concentrated under reduced pressure to give the object product (80 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. washa fraction eluted with ethyl acetate-hexane (8:2)
  7. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-6338b9aec3d94b69a0133018de69ee70
Source dataset
uspto-grants-2015_12
Patent number
US09221836B2

Reaction notes

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