Ethanol → HCID 53876278, compound

HRID 1421540Notes

Reaction equation

HRID 1421540 reaction equation
C(O)C.[F:4][C:5]1[CH:21]=[CH:20][C:8]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][S:18][CH3:19])=[CH:13][CH:12]=2)=O)=[CH:7][CH:6]=1.[C:22]([O:26][CH2:27][CH3:28])(=[O:25])[NH:23][NH2:24]>C(O)(=O)C>[CH2:27]([O:26][C:22]([NH:23][N:24]=[C:9]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][S:18][CH3:19])=[CH:13][CH:12]=1)[C:8]1[CH:20]=[CH:21][C:5]([F:4])=[CH:6][CH:7]=1)=[O:25])[CH3:28]

Participants

5

Reactant 3

HCID 702EthanolHCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 54099074HCID 54099074, compound

Product 1

HCID 53876278HCID 53876278, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

An ethanol solution (100 ml) of 4-fluoro-4'-methylmercaptomethylbenzophenone (7.8 g), ethyl carbazate (9.4 g) and acetic acid (9 ml) was heated for 20 hours with refluxing. The solvent was distilled off under reduced pressure, and then the obtained oily substance was diluted with dichloromethane, and washed successively with an aqueous 5% sodium hydroxide solution, water and an aqueous saturated sodium chloride solution, followed by drying over anhydrous magnesium sulfate. The solvent was then distilled off to obtain 4-fluoro-4'-methylmercaptomethylbenzophenone ethoxycarbonylhydrazone (6.4 g) as an isomer mixture.

Workup

  1. temperaturewith refluxing
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionthe obtained oily substance was diluted with dichloromethane
  4. washwashed successively with an aqueous 5% sodium hydroxide solution, water
  5. dry with materialby drying over anhydrous magnesium sulfate
  6. distillationThe solvent was then distilled off

Sources & evidence

ORD record
ord-8ecc727d12c540dd88738aafde0434c5
Source dataset
uspto-grants-2000_06
Patent number
US06077866

Reaction notes

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