Hydrazinecarboxylic acid, ethyl ester → 4-Chloro-4'-methylmercaptomethylbenzophenone ethoxycarbonylhydrazone

HRID 1421542Notes

Reaction equation

HRID 1421542 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][S:15][CH3:16])=[CH:10][CH:9]=2)=O)=[CH:4][CH:3]=1.[C:19]([O:23][CH2:24][CH3:25])(=[O:22])[NH:20][NH2:21]>C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(O)C>[CH2:24]([O:23][C:19]([NH:20][N:21]=[C:6]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][S:15][CH3:16])=[CH:10][CH:9]=1)[C:5]1[CH:17]=[CH:18][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:22])[CH3:25]

Participants

5

Reactant 2

HCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 196893654-Chloro-4'-methylthiomethylbenzophenone

Product 1

HCID 539729254-Chloro-4'-methylmercaptomethylbenzophenone ethoxycarbonylhydrazoneYield 86.4%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 702EthanolSolvent

Procedure

An ethanol solution (100 ml) of 4-chloro-4'-methylmercaptomethylbenzophenone (8.3 g), ethyl carbazate (10 g) and pyridinium p-toluenesulfonate (0.1 g) was heated for 16 hours with refluxing. After cooling to a room temperature, the reaction mixture was poured into ice water, and then the precipitated crystals were collected by filtration, and washed with water. After air-drying, 4-chloro-4'-methylmercaptomethylbenzophenone ethoxycarbonylhydrazone (9.4 g) was obtained as an isomer mixture.

Workup

  1. temperaturewith refluxing
  2. filtrationthe precipitated crystals were collected by filtration
  3. washwashed with water
  4. customAfter air-drying

Sources & evidence

ORD record
ord-26a8f36fbe80426e8e59c2e85d55cee4
Source dataset
uspto-grants-2000_06
Patent number
US06077866

Reaction notes

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