Phenylacetaldehyde → Dimethyl[2-(prop-2-yn-1-yloxy)ethyl]amine

HRID 871063

Reaktionsgleichung

Reaktionsgleichung von HRID 871063
[C:1]1([CH2:7][CH:8]=[O:9])C=CC=CC=1.[N+]([C:13]1C=CC=C[C:14]=1CC=O)([O-])=O.NN[C:24]([NH2:26])=S.[C-:27]#N.[Na+].[NH4+].[Cl-]>O.CO>[CH3:27][N:26]([CH3:24])[CH2:13][CH2:14][O:9][CH2:8][C:7]#[CH:1]

Komponenten

7

Edukt 5

HCID 998PhenylacetaldehydeHCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 2723789ThiosemicarbazideHCID 108447642-Nitrobenzeneacetaldehyde

Produkt 1

HCID 12336591Dimethyl[2-(prop-2-yn-1-yloxy)ethyl]amineAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22242641Methanol--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of the phenyl-acetaldehyde 1a or 2-nitro-phenyl-acetaldehyde 1b (8.3 mmol), thiosemicarbazide 2b (0.757 gr, 8.32 mmol) in H2O-methanol 55 ml (1:10 v/v) were added NaCN (0.624 g, 12.7 mmol) and NH4Cl (1.04 g, 19.44 mmol). The reaction mixture was stirred overnight at 50° C. The product from 1b was filtered, washed with cold water and dried under vacuum yielding 0.157 g (10%) of pure hydrazinecarbothioamide (3b). The precipitated crude product from 1a was purified on C18-reversed phase flash chromatography column employing a linear gradient of 0-30% A in B (flow-rate 40 mL/min), where A is 0.1% formic acid in CH3CN and B is 0.1% of formic acid in water, yielding 310 mg (15%) of pure 3b.

Aufarbeitung

  1. filtrationThe product from 1b was filtered
  2. washwashed with cold water
  3. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-fa033966e32d4968a836450545a428d2
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969573B2

Verknüpfte Notizen

Wird geladen…