p-Cyanobenzyl alcohol → N-Hydroxy-4-(hydroxymethyl)benzimidamide

HRID 1941874Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1941874
[OH:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.Cl.[NH2:12][OH:13].C([O-])(O)=O.[Na+]>CO>[OH:13][N:12]=[C:7]([NH2:8])[C:6]1[CH:9]=[CH:10][C:3]([CH2:2][OH:1])=[CH:4][CH:5]=1

Komponenten

5

Edukt 3

HCID 160549p-Cyanobenzyl alcoholHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Produkt 1

HCID 53437716N-Hydroxy-4-(hydroxymethyl)benzimidamideAusbeute 101,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

A solution of 4-(hydroxymethyl)benzonitrile (22.43 g, 0.1685 g), hydroxylamine hydrochloride (18.67 g, 0.2689 mol) and NaHCO3 (45.22 g, 0.538 mol) in methanol (250 mL) was heated to reflux overnight. Upon cooling, the heterogeneous mixture was filtered and the solids were washed with additional methanol. The filtrate was evaporated to dryness to afford an off-white solid. The solids were suspended in ˜75 mL hot methanol, then cooled to room temperature and filtered. The filtrate was evaporated to afford N′-hydroxy-4-(hydroxymethyl)benzimidamide (28.5 g) as a white solid. The material was used without further purification. The compound had an HPLC retention time=0.232 min. −Column: CHROMOLITH® SpeedROD 4.6×50 mm (4 min.); Solvent A=10% MeOH, 90% H2O, 0.2% H3PO4; Solvent B=90% MeOH, 10% H2O, 0.2% H3PO4. LC/MS M+1=167.3

Aufarbeitung

  1. temperatureto reflux overnight
  2. temperatureUpon cooling
  3. filtrationthe heterogeneous mixture was filtered
  4. washthe solids were washed with additional methanol
  5. customThe filtrate was evaporated to dryness
  6. customto afford an off-white solid
  7. filtrationfiltered
  8. customThe filtrate was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-a3bfb01f27d442ed8e07de3525291c7d
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389509B2

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