Hydrazine hydrate (1:1) → HCID 86739299, compound

HRID 1903048Notes

Reaction equation

HRID 1903048 reaction equation
[CH3:1][N:2]([CH3:21])[S:3]([NH:6][C:7]1[CH:8]=[C:9]([CH:18]=[CH:19][CH:20]=1)[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O)(=[O:5])=[O:4].O.[NH2:23][NH2:24]>C(O)C>[CH3:1][N:2]([CH3:21])[S:3]([NH:6][C:7]1[CH:8]=[C:9]([CH:18]=[CH:19][CH:20]=1)[C:10](=[N:23][NH2:24])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 13609461HCID 13609461, compound

Product 1

HCID 86739299HCID 86739299, compoundYield 109%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-[N-(dimethylaminosulfonyl)amino]-benzophenone (200 mg) and hydrazine hydrate (100 mg) in ethanol (4 ml) is refluxed for 17.5 hours. The reaction mixture is concentrated in vacuum and the residue is basified with aqueous sodium hydrogencarbonate and shaken with methylene chloride. The organic layer is washed with water, dried over anhydrous sodium sulfate and concentrated in vacuum. The residue is chromatographed on a column of silica gel, which is eluted with 3% methanol and methylene chloride. The eluate is concentrated in vacuum to give 3-[N-(dimethylaminosulfonyl)-amino]benzophenone hydrazone(228 mg) as an oil.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuum
  2. washThe organic layer is washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuum
  5. customThe residue is chromatographed on a column of silica gel, which
  6. washis eluted with 3% methanol and methylene chloride
  7. concentrationThe eluate is concentrated in vacuum

Sources & evidence

ORD record
ord-f945cd21c0534eed8c8aed35187954dd
Source dataset
uspto-grants-1984_03
Patent number
US04435394

Reaction notes

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