Triethylamine → (E)-2-(4-chloro-phenyl)-ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide

HRID 1272354Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1272354
[CH3:1][C:2]([NH:9][S:10]([CH:13]=[CH2:14])(=[O:12])=[O:11])([CH3:8])[CH2:3][C:4]([CH3:7])([CH3:6])[CH3:5].[Cl:15][C:16]1[CH:21]=[CH:20][C:19](OC)=[C:18](I)[CH:17]=1.C(N(CC)CC)C>CN(C)C=O.ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:8][C:2]([NH:9][S:10](/[CH:13]=[CH:14]/[C:19]1[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=1)(=[O:12])=[O:11])([CH3:1])[CH2:3][C:4]([CH3:5])([CH3:6])[CH3:7]

Komponenten

8

Edukt 3

HCID 8471TriethylamineHCID 28009784-Chloro-2-iodoanisoleHCID 17748074N-(2,4,4-Trimethylpentan-2-yl)ethenesulfonamide

Produkt 1

HCID 17748075(E)-2-(4-chloro-phenyl)-ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amideAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11776TriphenylphosphineKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

Ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide (8.5 g, 38.8 mmol) and 4-chloroiodoanisole (7.87 g, 33.0 mmol) was dissolved in N,N-dimethylformamide (65 ml). Palladium acetate (139 mg, 0.62 mmol) and triphenylphosphine (357 mg, 1.36 mmol) was added to the reaction followed by triethylamine (12.5 ml, 89.3 mmol). The reaction was flushed with nitrogen and heated at 140° C. for 16 hours. The reaction was cooled to room temperature and quenched with 1N HCl (250 ml). The aqueous solution was extracted with ethyl acetate (3×200 ml). The organic solution was dried over MgSO4, filtered and concentrated in vacuo to afford a solid. The solid was dissolved in dichloromethane and purified by dry flash chromatography (SiO2, heptane to 1:1 heptane: ethyl acetate). The fractions were combined to afford (E)-2-(4-chloro-phenyl)-ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide (5.0 g, 46% yield).

Aufarbeitung

  1. customThe reaction was flushed with nitrogen
  2. temperatureThe reaction was cooled to room temperature
  3. customquenched with 1N HCl (250 ml)
  4. extractionThe aqueous solution was extracted with ethyl acetate (3×200 ml)
  5. dry with materialThe organic solution was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford a solid
  9. custompurified
  10. dry with materialby dry flash chromatography (SiO2, heptane to 1:1 heptane: ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-d44128a8f7034191b481ad78c66e2f04
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07208526B2

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