Methanol → Benzenesulfonamide, N-benzyl-

HRID 855974

Reaktionsgleichung

Reaktionsgleichung von HRID 855974
[CH:1](=[N:8][S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[SiH](C)C1C=CC=CC=1.CO.FC(F)(F)C(O)=O>C1C=CC=CC=1.C(OCC)C>[C:12]1([S:9]([NH:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)(=[O:11])=[O:10])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Komponenten

7

Edukt 4

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 13014DimethylphenylsilaneHCID 555202N-Benzylidenebenzenesulfonamide

Produkt 1

HCID 95236Benzenesulfonamide, N-benzyl-Ausbeute 86,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

In a 5 mL flask opened to the air, to a clear solution of N-benzylidenebenzene sulfonamide (100 mg, 0.408 mmol) in benzene (0.4 mL) was added dimethylphenylsilane (125 μL, 0.816 mmol). The flask was placed in a 60° C. bath and iodo[bis(triphenylphosphine)] oxorhenium(V) (18 mg, 0.021 mmol) was added. The resulting brown solution was heated at 60° C. for 2 hours. To the reaction mixture was added methanol (0.4 mL) followed by trifluoroacetic acid (35 μL), and heating continued for an additional 2 h. The crude reaction mixture was directly applied to a SiO2 column and chromatographed eluting with 1:1 hexanes:diethyl ether to afford N-phenylsulfonylbenzylamine (87 mg, 86% yield) as a slightly yellow solid.

Aufarbeitung

  1. customwas placed in a 60° C.
  2. temperatureheating
  3. customThe crude reaction mixture
  4. customchromatographed
  5. washeluting with 1:1 hexanes

Quellen und Nachweise

ORD-Eintrag
ord-c194520253dd4b72993fd8bfa88af6c1
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07262315B2

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