Triethylamine → N-(2-(tert-butyldimethylsilyloxy)ethyl)-N-(2-chlorophenyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide

HRID 84413

Reaktionsgleichung

Reaktionsgleichung von HRID 84413
[Si:1]([O:8][CH2:9][CH2:10][NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[S:26]1[C:30]2[C:31]3[CH:39]=[CH:38][CH:37]=[CH:36][C:32]=3[O:33][CH2:34][CH2:35][C:29]=2[CH:28]=[C:27]1[C:40](Cl)=[O:41]>O1CCCC1>[Si:1]([O:8][CH2:9][CH2:10][N:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])[C:40]([C:27]1[S:26][C:30]2[C:31]3[CH:39]=[CH:38][CH:37]=[CH:36][C:32]=3[O:33][CH2:34][CH2:35][C:29]=2[CH:28]=1)=[O:41])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 579001474,5-Dihydrobenzo[b]thieno[2,3-d]oxepine-2-carbonylchlorideHCID 66868760N-(2-(tert-butyldimethylsilyloxy)ethyl)-2-chloroaniline

Produkt 1

HCID 57900150N-(2-(tert-butyldimethylsilyloxy)ethyl)-N-(2-chlorophenyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamideAusbeute 71,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of N-(2-(tert-butyldimethylsilyloxy)ethyl)-2-chloroaniline (0.145 g, 0.508 mmol) and triethylamine (0.113 mL, 0.812 mmol) in tetrahydrofuran (1 mL, 10 mmol) was added a solution of 4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carbonyl chloride (0.107 g, 0.406 mmol) in tetrahydrofuran (4 mL). The reaction was stirred overnight and concentrated in vacuo. Aqueous work up gave a yellow solid which was purified on silica by MPLC to give 150 mg of N-(2-(tert-butyldimethylsilyloxy)ethyl)-N-(2-chlorophenyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customAqueous work up gave a yellow solid which
  3. customwas purified on silica by MPLC

Quellen und Nachweise

ORD-Eintrag
ord-c1ffed0b9a24450082243ac2aaa200cf
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846762B2

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