Hydrochloric Acid → 4-(Biphenyl-2-yloxy)-3-cyanobenzenesulfonyl chloride

HRID 1692249

Reaktionsgleichung

Reaktionsgleichung von HRID 1692249
C(N[S:9]([C:12]1[CH:13]=[CH:14][C:15]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:16]([CH:19]=1)[C:17]#[N:18])(=[O:11])=[O:10])C1C=CC=CC=1.[ClH:33].Cl[O-].[Na+]>ClCCl>[C:22]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[O:20][C:15]1[CH:14]=[CH:13][C:12]([S:9]([Cl:33])(=[O:11])=[O:10])=[CH:19][C:16]=1[C:17]#[N:18]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 23665760Sodium HypochloriteHCID 669054565-Benzylsulfamyl-2-(biphenyl-2-yloxy)-benzonitrile

Produkt 1

HCID 594365064-(Biphenyl-2-yloxy)-3-cyanobenzenesulfonyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 5-benzylsulfamyl-2-(biphenyl-2-yloxy)-benzonitrile (Preparation 56, 6.06 g, 15.4 mmol), dichloromethane and aq HCl was stirred vigorously with cooling (ice bath). Sodium hypochlorite was added dropwise over 30 minutes and stirring continued with cooling for 1 hour. The layers were separated, the aqueous extracted with dichloromethane (2×100ml), and the organic collected, dried (MgSO4) and concentrated in vacuo. The residue was purified using silica gel column chromatography (ethyl acetate:Heptane 10/90 to 20/80) to furnish 4.58 g of the title compound. 1HNMR (CDCl3): δ 6.7 (m, 1H), 7.2-7.6 (m, 9H), 7.85 (m, 1H), 8.15 (m, 1H).

Aufarbeitung

  1. temperaturewith cooling (ice bath)
  2. stirringstirring
  3. temperaturewith cooling for 1 hour
  4. customThe layers were separated
  5. extractionthe aqueous extracted with dichloromethane (2×100ml)
  6. dry with materialthe organic collected, dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-5c129350de4b462fbbb0f4d8097ae05a
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153814B2

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