Sodium Hydroxide → Carbamodithioic acid, bis(1-methylethyl)-, 4-amino-3-pyridinyl ester

HRID 2366164Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2366164
[CH:1]([N:4]([CH:21]([CH3:23])[CH3:22])[C:5]([S:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[NH:14]C(=O)C(C)(C)C)=[S:6])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[CH:21]([N:4]([CH:1]([CH3:3])[CH3:2])[C:5]([S:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[NH2:14])=[S:6])([CH3:23])[CH3:22]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 14062657HCID 14062657, Verbindung

Produkt 1

HCID 11437145Carbamodithioic acid, bis(1-methylethyl)-, 4-amino-3-pyridinyl esterAusbeute 100,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A mixture of 4-pivalamidopyridin-3-yl diisopropylcarbamodithioate (5.0 g, 14 mmol) and NaOH (1.1 g, 28 mmol) in MeOH (100 mL) was stirred at 20° C. for 20 hours. The reaction was concentrated under reduced pressure and the residue was purified by silica gel column chromatography, eluting with EtOAc/petroleum ether (1:8) to give the desired product as a white solid (3.8 g, 93% yield). 1H NMR (500 MHz, CDCl3): δ 8.24 (t, J=2.0 Hz, 1H), 6.69 (d, J=5.5 Hz, 1H), 4.90 (s, 2H), 1.64-1.30 (m, 14H). LCMS (ESI) m/z: 270.1 [M+H+].

Aufarbeitung

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography
  3. washeluting with EtOAc/petroleum ether (1:8)

Quellen und Nachweise

ORD-Eintrag
ord-c535dfbab0df423893d8bf654a183390
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697708B2

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