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

HRID 1949730

Reaktionsgleichung

C([Li])CCC.Br[C:7]1[S:20][C:10]2[C:11]3[CH:19]=[N:18][CH:17]=[CH:16][C:12]=3[O:13][CH2:14][CH2:15][C:9]=2[CH:8]=1.[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]=[C:29]=[O:30].Cl.C([O-])(O)=O.[Na+]>CCCCCC.O1CCCC1>[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH:28][C:29]([C:7]1[S:20][C:10]2[C:11]3[CH:19]=[N:18][CH:17]=[CH:16][C:12]=3[O:13][CH2:14][CH2:15][C:9]=2[CH:8]=1)=[O:30]

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

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.

Aufarbeitung

waitthe mixture was kept at −78° C. for 20 min
extractionThe mixture was extracted twice with methylene chloride
washwashed with water and brine
dry with materialdried over MgSO4
concentrationAfter concentrating under vacuum
customthe residue was triturated with ethyl acetate

Quellen und Nachweise

ORD-Eintrag: ord-559b57addca246af8863176710f0d9bb
Quelldatensatz: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08399690B2

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