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

HRID 1421541Notes

Reaction equation

HRID 1421541 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][S:15]([CH3:17])=[O:16])=[CH:10][CH:9]=2)=O)=[CH:4][CH:3]=1.[C:20]([O:24][CH2:25][CH3:26])(=[O:23])[NH:21][NH2:22]>C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(O)C>[CH2:25]([O:24][C:20]([NH:21][N:22]=[C:6]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][S:15]([CH3:17])=[O:16])=[CH:10][CH:9]=1)[C:5]1[CH:18]=[CH:19][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:23])[CH3:26]

Participants

5

Reactant 2

HCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 187798984-Chloro-4'-methylsulfinylmethylbenzophenone

Product 1

HCID 541481014-Chloro-4'-methylsulfinylmethylbenzophenone ethoxycarbonylhydrazoneYield 85.3%

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'-methylsulfinylmethyl benzophenone (5.8 g), ethyl carbazate (6.3 g) and pyridinium p-toluenesulfonate (0.1 g) was heated for 6 hours with refluxing. After cooling to a room temperature, the reaction mixture was poured into ice-water, and the precipitated crystals were collected by filtration, and washed successively with an aqueous sodium bicarbonate solution and water. After air-drying, 4-chloro-4'-methylsulfinylmethylbenzophenone ethoxycarbonylhydrazone (6.4 g) was obtained as an isomer mixture.

Workup

  1. temperaturewith refluxing
  2. filtrationthe precipitated crystals were collected by filtration
  3. washwashed successively with an aqueous sodium bicarbonate solution and water
  4. customAfter air-drying

Sources & evidence

ORD record
ord-4aff65363cfc438091dc88e74ec5672e
Source dataset
uspto-grants-2000_06
Patent number
US06077866

Reaction notes

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