Triphenylphosphine → N-cyclopropyl-N-[1-(2-naphthyl)ethyl]-2-nitrobenzenesulfonamide

HRID 922434

Reaktionsgleichung

Reaktionsgleichung von HRID 922434
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11](O)[CH3:12].[CH:14]1([NH:17][S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[N+:27]([O-:29])=[O:28])(=[O:20])=[O:19])[CH2:16][CH2:15]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH:14]1([N:17]([CH:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[CH3:12])[S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[N+:27]([O-:29])=[O:28])(=[O:20])=[O:19])[CH2:16][CH2:15]1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 98243alpha-Methylnaphthalene-2-methanolHCID 796630N-cyclopropyl-2-nitrobenzenesulfonamide

Produkt 1

HCID 86707860N-cyclopropyl-N-[1-(2-naphthyl)ethyl]-2-nitrobenzenesulfonamideAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1-(2-naphthyl)ethanol (344 mg), N-cyclopropyl-2-nitrobenzenesulfonamide (581 mg) and triphenylphosphine (787 mg) in tetrahydrofuran (10 mL) was added dropwise diisopropyl azodicarboxylate (590 μL) under ice-cooling, and the mixture was stirred at room temperature for 3 hours. The reaction solution was concentrated, and the resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1→1/1), and then triturated with diethyl ether-n-hexane (1:1) to give N-cyclopropyl-N-[1-(2-naphthyl)ethyl]-2-nitrobenzenesulfonamide j[REx(1-1)] (499 mg) as a colorless powder.

Aufarbeitung

  1. temperaturecooling
  2. concentrationThe reaction solution was concentrated
  3. customthe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1→1/1)
  4. customtriturated with diethyl ether-n-hexane (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-ee73abe846394dbf8b14aa530845d304
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278944B2

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