Reaktionsgleichung
O(CCCC(O)=O)C1C=CC=CC=1.[N:14]1[C:23]2[C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[O:20][CH2:19][CH2:18][C:17]=2[S:16][C:15]=1[C:28]([OH:30])=O.[OH-].[Na+].[Cl:33][C:34]1[CH:41]=[CH:40][CH:39]=[CH:38][C:35]=1[NH:36][CH3:37]>C1COCC1.O>[Cl:33][C:34]1[CH:41]=[CH:40][CH:39]=[CH:38][C:35]=1[N:36]([CH3:37])[C:28]([C:15]1[S:16][C:17]2[CH2:18][CH2:19][O:20][C:21]3[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=3[C:23]=2[N:14]=1)=[O:30]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
To a solution of 4-bromo-3,4-dihydro-2H-benzo[b]oxepin-5-one (4.0 g, 12.4 mmol) in ethanol, was added ethyl thiooxamate (5.0 g, 37.4 mmol) and the reaction mixture was heated to reflux for 3 days. Purification on silica gave 4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid ethyl ester, which was hydrolyzed to the carboxylic acid, 4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid, in THF, sodium hydroxide, and water. 4,5-Dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid was coupled with 2-chloro-N-methylaniline using General Procedure B. Purification on silica gave 226. 1H NMR (400 MHz, CDCl3): 3.24 (2H, t), 3.37 (3H, s), 4.17-4.25 (2H, m), 6.74-6.79 (1H, m), 6.85 (1H, dd), 7.02-7.07 (1H, m), 7.11 (1H, dd), 7.27-7.33 (3H, m), 7.42-7.45 (1H, m). MS: (ESI+) MH 371
Aufarbeitung
- customPurification on silica
Quellen und Nachweise
- ORD-Eintrag
- ord-92bc6a195ef84da49a114f65fbd21a68
- Quelldatensatz
- uspto-grants-2014_09
- Patentnummer
- US08846762B2
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