Sodium Hydroxide → 1-(3-(Benzyloxy)-5-bromopyridin-2-yl)thiourea

HRID 1426082Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1426082
C([NH:9][C:10]([NH:12][C:13]1[C:18]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:17][C:16]([Br:27])=[CH:15][N:14]=1)=[S:11])(=O)C1C=CC=CC=1.[OH-].[Na+]>O>[CH2:20]([O:19][C:18]1[C:13]([NH:12][C:10]([NH2:9])=[S:11])=[N:14][CH:15]=[C:16]([Br:27])[CH:17]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 866396501-Benzoyl-3-(3-(benzyloxy)-5-bromopyridin-2-yl)thiourea

Produkt 1

HCID 727056401-(3-(Benzyloxy)-5-bromopyridin-2-yl)thioureaAusbeute 92,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A 1 L round-bottom flask was charged with 1-benzoyl-3-(3-(benzyloxy)-5-bromopyridin-2-yl)thiourea (17.9 g, 40.5 mmol) and 3M sodium hydroxide (3.3 mL, 9.9 mmol), and the reaction mixture was refluxed overnight. The reaction mixture was then cooled, poured into water, and filtered to provide 1-(3-(benzyloxy)-5-bromopyridin-2-yl)thiourea (12.6 g, 92.2% yield) as a yellow solid. 1H NMR (CDCl3) δ 10.60 (bs, 1H), 8.59 (bs, 1H), 7.87 (d, 1H), 7.40 (m, 5H), 7.30 (d, 1H), 6.90 (m, 1H), 5.15 (s, 2H). Mass spectrum (apci) m/z=340.0 (M+H).

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed overnight
  2. temperatureThe reaction mixture was then cooled
  3. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-8fc37007cb4b49b8be39c803ddc45e07
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933077B2

Notizen zur Reaktion

Wird geladen…