Sodium Bicarbonate → 3-(8-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-4-(2-chlorophenyl)-1H-1,2,4-triazol-5(4H)-one

HRID 84567Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 84567
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[S:12][C:13]([C:15](=[N:24][NH2:25])[NH:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[Cl:23])=[CH:14][C:10]=3[CH2:9][CH2:8][O:7][C:6]=2[CH:26]=1.[C:27](C1NC=CN=1)(C1NC=CN=1)=[O:28].C(=O)(O)[O-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[S:12][C:13]([C:15]4[N:16]([C:17]5[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=5[Cl:23])[C:27](=[O:28])[NH:25][N:24]=4)=[CH:14][C:10]=3[CH2:9][CH2:8][O:7][C:6]=2[CH:26]=1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 178514378HCID 178514378, Verbindung

Produkt 1

HCID 579001113-(8-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-4-(2-chlorophenyl)-1H-1,2,4-triazol-5(4H)-oneAusbeute 56,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of crude 8-bromo-N-(2-chlorophenyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carbohydrazonamide (about 1.15 mmol) in dry THF (10 mL) was added carbonyl diimidazole (373 mg, 2.3 mmol). The reaction mixture was stirred at room temperature until completion judged by LCMS. Aqueous sodium bicarbonate was added and the mixture extracted with ethyl acetate. The combined organics were washed with brine, dried over sodium sulfate, concentrated and the residue purified by flash column chromatography (10-100% ethyl acetate in hexanes) to give 279 as a colorless solid (308 mg). 1H NMR (dmso-d6, 400 MHz) δ 12.32 (s, 1H), 7.75-7.59 (m, 4H), 7.42 (m, 1H), 7.27-7.21 (m, 2H), 6.53 (s, 1H), 4.21 (t, 2H), 2.97 (t, 2H). MS (ESI) 476.0.

Aufarbeitung

  1. extractionthe mixture extracted with ethyl acetate
  2. washThe combined organics were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customthe residue purified by flash column chromatography (10-100% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-dcea8805e2b74a05b4e74a02da3932cf
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846762B2

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