Potassium Carbonate → {4-[(2-Amino-2-oxoethyl)thio]phenyl}boronic acid

HRID 423533Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 423533
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]([OH:10])[OH:9])=[CH:4][CH:3]=1.Br[CH2:12][C:13]([NH2:15])=[O:14].C([O-])([O-])=O.[K+].[K+]>CC#N>[NH2:15][C:13](=[O:14])[CH2:12][S:1][C:2]1[CH:7]=[CH:6][C:5]([B:8]([OH:10])[OH:9])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 44318944-Mercaptophenylboronic acid

Produkt 1

HCID 66673418{4-[(2-Amino-2-oxoethyl)thio]phenyl}boronic acidAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 4-mercaptophenylboronic acid (1.0 g, 90%, 5.84 mmol), 2-bromoacetamide (1.8 g, 13 mmol) and K2CO3 (2.70 g, 19.5 mmol) in CH3CN (20 mL) was stirred at ambient temperature overnight. After CH3CN was removed, water was added to the residue, and the solid was collected via filtration and washed with water to give 0.6 g (49%) of {4-[(2-amino-2-oxoethyl)thio]phenyl}boronic acid as a white solid. The boronic acid was used without further purification. 1H NMR (400 MHz, DMSO-d6): δ 8.00 (s, 2H), 7.68 (d, 2H, J=8.2 Hz), 7.55 (bs, 1H), 7.24 (d, 2H, J=8.2 Hz), 7.15 (bs, 1H), 3.61 (s, 2H); LRMS (APCI), m/z 210 (M−H).

Aufarbeitung

  1. customAfter CH3CN was removed
  2. additionwater was added to the residue
  3. filtrationthe solid was collected via filtration
  4. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-cc96d83cf8c44c2f95e2db6ce75b7cac
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101634B2

Notizen zur Reaktion

Wird geladen…