O-Methylhydroxylamine hydrochloride → HCID 53659825, compound

HRID 1903049Notes

Reaction equation

HRID 1903049 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].Cl.[CH3:23][O:24][NH2:25]>C(O)C>[CH3:23][O:24][N:25]=[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:9]1[CH:18]=[CH:19][CH:20]=[C:7]([NH:6][S:3]([N:2]([CH3:21])[CH3:1])(=[O:5])=[O:4])[CH:8]=1

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 13609461HCID 13609461, compound

Product 1

HCID 53659825HCID 53659825, compoundYield 107.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-[N-(dimethylaminosulfonyl)amino]-benzophenone (500 mg) and O-methylhydroxylamine hydrochloride (830 mg) in ethanol (10 ml) is refluxed for 19 hours, and the resultant mixture is concentrated in vacuum. 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-methylene chloride. The eluate is concentrated in vacuum to give 3-[N-(dimethylaminosulfonyl)amino]benzophenone O-methyloxime (590 mg) as an oil.

Workup

  1. concentrationthe resultant 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-methylene chloride
  7. concentrationThe eluate is concentrated in vacuum

Sources & evidence

ORD record
ord-f64b5714b5204ff9ac6d2e0cf8c9c915
Source dataset
uspto-grants-1984_03
Patent number
US04435394

Reaction notes

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