Hydroxyamine hydrochloride → N-[4-[(E)-N'-hydroxycarbamimidoyl]-2-(trifluoromethoxy)phenyl]acetamide

HRID 722220Notes

Reaction equation

HRID 722220 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:12])[CH3:11])=[C:5]([O:13][C:14]([F:17])([F:16])[F:15])[CH:4]=1)#[N:2].Cl.[NH2:19][OH:20].C([O-])(=O)C.[Na+]>C(O)(C)C>[OH:20][NH:19][C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:12])[CH3:11])=[C:5]([O:13][C:14]([F:15])([F:17])[F:16])[CH:4]=1)=[NH:2]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 2736739N-[4-cyano-2-(trifluoromethoxy)phenyl]acetamide

Product 1

HCID 178474202N-[4-[(E)-N'-hydroxycarbamimidoyl]-2-(trifluoromethoxy)phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The mixture consisting of 610 mg of N-(4-cyano-2-trifluoromethoxyphenyl)-acetamide, 15 ml of isopropanol, 255 mg of hydroxylamine hydrochloride and 410 mg of sodium acetate was heated to reflux for 5 hours. After cooling, the insoluble fraction was filtered off, and the filtrate is concentrated and taken up in a little isopropanol, the product was precipitated, filtered off with suction and dried by adding water until the first cloudiness and subsequent stirring.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 hours
  3. temperatureAfter cooling
  4. filtrationthe insoluble fraction was filtered off
  5. concentrationthe filtrate is concentrated
  6. customthe product was precipitated
  7. filtrationfiltered off with suction
  8. customdried
  9. additionby adding water until the first cloudiness and subsequent stirring

Sources & evidence

ORD record
ord-1f11f194038843a2aceb9383d2ab28a4
Source dataset
uspto-grants-2006_11
Patent number
US07138414B2

Reaction notes

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