Dimethylformamide → 9-Bromo-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carbonyl chloride

HRID 575015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 575015
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:14][CH2:13][CH2:12][N:11]3[C:7](=[N:8][C:9]([C:15](O)=[O:16])=[CH:10]3)[C:6]=2[CH:18]=1.C(Cl)(C([Cl:23])=O)=O.CN(C)C=O>C(#N)C.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:14][CH2:13][CH2:12][N:11]3[C:7](=[N:8][C:9]([C:15]([Cl:23])=[O:16])=[CH:10]3)[C:6]=2[CH:18]=1

Komponenten

6

Edukt 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 7174327210-Bromo-5,6-dihydrobenzo[F]imidazo[1,2-D][1,4]oxazepine-2-carboxylic acid

Produkt 1

HCID 866930509-Bromo-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carbonyl chlorideAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Into a 10000-mL 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed a solution of 9-Bromo-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carboxylic acid (450 g, 1.46 mol, 1.00 equiv) in ACN (4500 mL), followed by the addition of (COCl)2 (450 mL) dropwise with stirring at 0° C. over 45 min. To this was added N,N-dimethylformamide (5 mL). The resulting solution was stirred at room temperature for 7 h, diluted with 2000 mL of DCM and concentrated under vacuum to afford 450 g (94%) of 9-Bromo-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carbonyl chloride as a gray solid.

Aufarbeitung

  1. customInto a 10000-mL 4-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. stirringThe resulting solution was stirred at room temperature for 7 h
  4. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-478956f1ef89460091dc0076f6dc2410
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09034866B2

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