Hydroxyamine hydrochloride → HCID 13609486, compound

HRID 1903047Notes

Reaction equation

HRID 1903047 reaction equation
[CH3:1][N:2]([CH3:23])[S:3]([NH:6][C:7]1[CH:8]=[C:9]([CH:20]=[CH:21][CH:22]=1)[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=O)(=[O:5])=[O:4].Cl.[NH2:25][OH:26]>C(O)C>[CH3:1][N:2]([CH3:23])[S:3]([NH:6][C:7]1[CH:8]=[C:9]([CH:20]=[CH:21][CH:22]=1)/[C:10](=[N:25]/[OH:26])/[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 13609465N'-[3-(4-Methoxybenzoyl)phenyl]-N,N-dimethylsulfuric diamide

Product 1

HCID 13609486HCID 13609486, compoundYield 17.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-[N-(dimethylaminosulfonyl)-amino]-4'-methoxybenzophenone (9 g) in ethanol (180 ml) is added hydroxylamine hydrochloride (11.23 g), and the resultant mixture is refluxed for 7 hours. The reaction mixture is concentrated in vacuum, and the residue is basified with aqueous sodium hydrogencarbonate and shaken with methylene chloride. The methylene chloride 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 20% methanolmethylene chloride. The eluate is concentrated in vacuum to give a crystalline product, which is washed with hot isopropyl ether to give a mixture of (Z)- and (E)-isomers (8.5 g). The mixture is crystallized from ethyl acetateisopropyl ether to give (E)-3-[N-(dimethylaminosulfonyl)-amino]-4'-methoxybenzophenone oxime (1.63 g) as crystals melting at 162° to 164° C.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuum
  2. washThe methylene chloride 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 20% methanolmethylene chloride
  7. concentrationThe eluate is concentrated in vacuum
  8. customto give a crystalline product, which
  9. washis washed with hot isopropyl ether
  10. customto give
  11. customThe mixture is crystallized from ethyl acetateisopropyl ether

Sources & evidence

ORD record
ord-8f2f0a10dca44f8e92a01c506f1cb072
Source dataset
uspto-grants-1984_03
Patent number
US04435394

Reaction notes

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