Water → HCID 23508484, compound

HRID 1883676Notes

Reaction equation

HRID 1883676 reaction equation
[C:1]1([NH:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9](OC(=O)C)(=[O:11])[CH3:10].[CH3:16][O:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1.O>N1C=CC=CC=1>[C:9]([NH:8][N:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:22](=[O:23])[C:21]1[CH:25]=[CH:26][C:18]([O:17][CH3:16])=[CH:19][CH:20]=1)(=[O:11])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 7477p-Anisoyl chlorideHCID 7516PhenylhydrazineHCID 7918Acetic Anhydride

Product 1

HCID 23508484HCID 23508484, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.08 g of phenylhydrazine was dissolved in 10 ml of pyridine, and 0.78 g of acetic anhydride was added thereto under cooling with ice, followed by stirring for 20 minutes. Then, 2.0 g of 4-methoxybenzoyl chloride was added thereto, followed by stirring at room temperature for 15 hours. After water was added to the reaction mixture, the product was extracted with ethyl acetate. The organic layer was washed with 5% hydrochloric acid and a 5% aqueous solution of sodium hydroxide, and dried over anhydrous sodium sulfate. After the solvent was distilled off, the resulting crude product was purified by silica gel column chromatography (using a 40:1 mixture of chloroform and methanol as the eluent) to obtain 1.0 g of N′-acetyl-4-methoxy-N-phenylbenzohydrazide.

Workup

  1. temperatureunder cooling with ice
  2. stirringby stirring at room temperature for 15 hours
  3. extractionthe product was extracted with ethyl acetate
  4. washThe organic layer was washed with 5% hydrochloric acid
  5. dry with materiala 5% aqueous solution of sodium hydroxide, and dried over anhydrous sodium sulfate
  6. distillationAfter the solvent was distilled off
  7. customthe resulting crude product was purified by silica gel column chromatography (
  8. additiona 40:1 mixture of chloroform and methanol as the eluent)

Sources & evidence

ORD record
ord-8783f07cbaeb409a90167cdce6bb584f
Source dataset
uspto-grants-2004_07
Patent number
US06762205B1

Reaction notes

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