Chlorosulfonic acid → 3-Trifluoroacetyl-1,2,4,5-tetrahydro-3-benzazepine-7-sulfonyl chloride

HRID 343315Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 343315
[Cl:1][S:2]([OH:5])(=O)=[O:3].[F:6][C:7]([F:22])([F:21])[C:8]([N:10]1[CH2:16][CH2:15][C:14]2[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=2[CH2:12][CH2:11]1)=[O:9]>ClCCl>[F:22][C:7]([F:6])([F:21])[C:8]([N:10]1[CH2:11][CH2:12][C:13]2[CH:20]=[CH:19][C:18]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:17][C:14]=2[CH2:15][CH2:16]1)=[O:9]

Komponenten

4

Edukt 2

HCID 24638Chlorosulfonic acidHCID 218871391-(4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)-2,2,2-trifluoroethanone

Produkt 1

HCID 542865763-Trifluoroacetyl-1,2,4,5-tetrahydro-3-benzazepine-7-sulfonyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Chlorosulphonic acid (10.4 ml, 0.156 mol) was added dropwise to a stirred, cold solution of the product from (b) above (5.85 g, 11.7 mmol) in dichloromethane, whilst ensuring that the temperature of the reaction mixture was held between -12 and -8° C. After 2 days at room temperature, the reaction solution was poured onto ice and the aqueous phase separated and extracted with dichloromethane. The combined organic extracts were dried (MgSO4) and evaporated under reduced pressure to provide an oil (7.9 g) which was purified by chromatography on silica gel, using a mixture of hexane and ether (1:3) as eluent, to give the title compound as a colourless oil which eventually solidified. Crystallisation of a sample from diisopropyl ether produced a white solid, m.p. 87°-88° C. Found: C,41.75; H,3.18; N,3.92. C12H11F3ClNO3S requires C,42.17; H,3.24; N,4.10%.

Aufarbeitung

  1. customwas held between -12 and -8° C
  2. additionthe reaction solution was poured onto ice
  3. customthe aqueous phase separated
  4. extractionextracted with dichloromethane
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-449140633ad045838f11624ec3d0dec3
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05861393

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