Reaktion #171649

Reaktionsgleichung

HCl

n-Butyllithium

2-bromo-4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepine

1-Chloro-2-isocyanato-benzene

NaHCO3

→

N-(2-chlorophenyl)-4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepin-2-carboxamide

Ausbeute 66.2%

Lösungsmittel

hexane

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITthe mixture was kept at −78° C. for 20 min
2. 2
   ExtraktionThe mixture was extracted twice with methylene chloride
3. 3
   Waschenwashed with water and brine
4. 4
   Trocknendried over MgSO4
5. 5
   EinengenAfter concentrating under vacuum
6. 6
   Sonstigethe residue was triturated with ethyl acetate

Vorschrift

1.6 M of n-Butyllithium in hexane (0.6302 mL) was added dropwise to a solution of 2-bromo-4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepine (0.227 g, 0.804 mmol) in tetrahydrofuran (6.00 mL, 74.0 mmol) at −75° C. The dark brown mixture was stirred at −78° C. for 20 min. 1-Chloro-2-isocyanato-benzene (0.1421 g, 0.9252 mmol) in 2 ml of tetrahydrofuran was added dropwise and the mixture was kept at −78° C. for 20 min. 4N aq. HCl (1 ml) was added and the mixture was poured into 50 ml of sat. aq NaHCO3. The mixture was extracted twice with methylene chloride, combined, and washed with water and brine, and dried over MgSO4. After concentrating under vacuum, the residue was triturated with ethyl acetate. The collected precipitate was N-(2-chlorophenyl)-4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepin-2-carboxamide (0.19 g, 66% yield). MS (ESI+) 357.0.

Quelle