Ethyl Acetate → [4-(Methanesulfonylaminocarbonyl)butyl]triphenylphosphonium bromide

HRID 561773

Reaktionsgleichung

Reaktionsgleichung von HRID 561773
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])=[O:26].C(OCC)(=O)C.CC(C)=O.C(OCC)(=O)C>C1(C)C(C)=CC=CC=1>[Br-:20].[CH3:31][S:28]([NH:27][C:25](=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21][P+:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)(=[O:30])=[O:29]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 202961415-Bromo-N-methanesulfonylpentanamideHCID 21584569Ethylacetate acetone

Produkt 1

HCID 19608840[4-(Methanesulfonylaminocarbonyl)butyl]triphenylphosphonium bromideAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

A stirring mixture consisting of triphenylphosphine (13.2 g, 24.4 mmol) and 5-bromo-N-(methylsulfonyl)pentanamide (prepared in Step A, 5.55 g, 21.5 mmol) in xylene (15 mL) was brought to reflux for 4 hours. Subsequently, ethyl acetate was added to the hot reaction mixture and stirring was continued for the next 15 minutes. The crude product was isolated from acetone-ethyl acetate to afford the title intermediate (8.68 g, 78%); melting point 189-190° C.

Aufarbeitung

  1. temperatureto reflux for 4 hours
  2. customwas continued for the next 15 minutes

Quellen und Nachweise

ORD-Eintrag
ord-62de46e6eef545028d030342528bad0f
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063240B2

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