Methyl iodide → HCID 56834371, Verbindung

HRID 1190508Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1190508
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[S:12][C:13]([C:15]([NH:17][C:18]4[CH:19]=[C:20]([CH:25]=[CH:26][C:27]=4[Cl:28])[C:21]([O:23][CH3:24])=[O:22])=[O:16])=[CH:14][C:10]=3[CH2:9][CH2:8][O:7][C:6]=2[CH:29]=1.[C:30]([O-])([O-])=O.[Cs+].[Cs+].CI>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[S:12][C:13]([C:15]([N:17]([C:18]4[CH:19]=[C:20]([CH:25]=[CH:26][C:27]=4[Cl:28])[C:21]([O:23][CH3:24])=[O:22])[CH3:30])=[O:16])=[CH:14][C:10]=3[CH2:9][CH2:8][O:7][C:6]=2[CH:29]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 56834370Methyl 3-(8-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamido)-4-chlorobenzoate

Produkt 1

HCID 56834371HCID 56834371, VerbindungAusbeute 94,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of methyl 3-(8-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamido)-4-chlorobenzoate (32 g, 65 mmol) and Cs2CO3 (42.4 g, 130 mmol) in DMF (500 mL) was added CH3I (12 mL, 195 mmol). The reaction mixture was stirred at room temperature overnight. Then it was concentrated to remove the DMF, and water was added into the mixture. The resulting precipitate was filtrated, washed by water, and dried to give methyl 3-(8-bromo-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamido)-4-chlorobenzoate (31 g, 94%) 1H NMR (CDCl3, 400 MHz): δ8.07-7.08 (m, 6H, ArH), 6.81 (s, 1H, ═CH), 4.22 (t, J=5.2 Hz, 2H, CH2), 3.94 (s, 3H, OCH3), 3.40 (s, 3H, NCH3), 3.01 (t, J=5.2 Hz, 2H, CH2)

Aufarbeitung

  1. concentrationThen it was concentrated
  2. customto remove the DMF, and water
  3. additionwas added into the mixture
  4. filtrationThe resulting precipitate was filtrated
  5. washwashed by water
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-0594d25d9fc24090a4feab0e10474011
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673952B2

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