Cyanogen Bromide → 5-(8-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-4-(2-chlorophenyl)-4H-1,2,4-triazol-3-amine

HRID 1949837Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1949837
[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.[N:27]#[C:28]Br>CO>[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:28]([NH2:27])=[N:25][N:24]=4)=[CH:14][C:10]=3[CH2:9][CH2:8][O:7][C:6]=2[CH:26]=1

Komponenten

4

Edukt 2

HCID 10476Cyanogen BromideHCID 178514378HCID 178514378, Verbindung

Produkt 1

HCID 579002025-(8-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-4-(2-chlorophenyl)-4H-1,2,4-triazol-3-amineAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

A solution of crude 8-bromo-N-(2-chlorophenyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carbohydrazonamide (195, 0.434) in methanol (5 mL) was treated with a solution of cyanogen bromide (115 mg, 1.1 mmol) in methanol (1 mL) at room temperature. The reaction vessel was sealed and heated at 45° C. for 2 h, cooled to room temperature, quenched upon addition of saturated sodium bicarbonate and extracted with ethylacetate. The combined organics were dried over sodium sulfate and concentrated and the residue purified by flash column chromatography (1-10% MeOH in methylene chloride to give 287 (43 mg, 21% yield). MS (ESI): 475.0

Aufarbeitung

  1. customThe reaction vessel was sealed
  2. temperaturecooled to room temperature
  3. customquenched upon addition of saturated sodium bicarbonate
  4. extractionextracted with ethylacetate
  5. dry with materialThe combined organics were dried over sodium sulfate
  6. concentrationconcentrated
  7. customthe residue purified by flash column chromatography (1-10% MeOH in methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-b6606eb7c9b74605b9fb8a6706aec9b7
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399690B2

Notizen zur Reaktion

Wird geladen…