p-Toluenesulfonic acid → Ethyl [2-(4-methoxyphenyl)-1-phenylethylidene]hydrazine carboxylate

HRID 2372359Notes

Reaction equation

HRID 2372359 reaction equation
[C:1]1([C:7](=O)[CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18]([O:22][CH2:23][CH3:24])(=[O:21])[NH:19][NH2:20].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][C:7](=[N:20][NH:19][C:18]([O:22][CH2:23][CH3:24])=[O:21])[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 2310922-(4-Methoxyphenyl)-1-phenylethan-1-one

Product 1

HCID 54026400Ethyl [2-(4-methoxyphenyl)-1-phenylethylidene]hydrazine carboxylateYield 76.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1-phenyl-2-(4-methoxyphenyl)-ethanone (Aldrich) (22.6 g, 0.1 mol), ethyl carbazate (12.5 g, 0.12 mol) and a spatula tip of TsOH in toluene (200 ml) was heated to reflux, and water was azeotropically removed. The reaction was complete (by TLC) after 4 hours. The solvent was removed under reduced pressure, and the crude solid was chromatographed, SiO2 (400 g), eluting with Hex/EtOAc, 7/3, affording 9 (24.0 g, 76.9%).

Workup

  1. temperatureto reflux
  2. customwater was azeotropically removed
  3. customafter 4 hours
  4. customThe solvent was removed under reduced pressure
  5. customthe crude solid was chromatographed
  6. washSiO2 (400 g), eluting with Hex/EtOAc, 7/3

Sources & evidence

ORD record
ord-544c1ec0d702451db3f04c2e01233c8a
Source dataset
uspto-grants-1992_03
Patent number
US05098918

Reaction notes

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