Triethylamine → N-(4-Nitrobenzyl)cyclopropanesulfonamide

HRID 576909

Reaktionsgleichung

Reaktionsgleichung von HRID 576909
Cl.[N+:2]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][CH:6]=1)([O-:4])=[O:3].[CH:13]1([S:16](Cl)(=[O:18])=[O:17])[CH2:15][CH2:14]1.C(N(CC)CC)C>ClCCl.Cl.O>[CH:13]1([S:16]([NH:10][CH2:9][C:8]2[CH:7]=[CH:6][C:5]([N+:2]([O-:4])=[O:3])=[CH:12][CH:11]=2)(=[O:18])=[O:17])[CH2:15][CH2:14]1

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 2760919Cyclopropanesulfonyl chlorideHCID 112524674-Nitrobenzylamine hydrochloride

Produkt 1

HCID 66910210N-(4-Nitrobenzyl)cyclopropanesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-Nitrobenzylamine HCl (1.5 g), cyclopropanesulfonyl chloride (1 g) and triethylamine (3 mL) were dissolved in dichloromethane (20 mL). The reaction solution was stirred at rt overnight. The reaction mixture was diluted with 1N HCl aq. solution (50 mL) and water (100 mL). The solution was extracted with ethyl acetate (2×100 mL). The organic solution was evaporated to give N-cyclopropylsulfonyl-4-nitrobenzylamine. 1H NMR (DMSO-d6): δ 0.89 (d, J=7.8 Hz, 4H), 4.33 (d, J=6.6 Hz, 2H), 7.61 (d, J=8.7 Hz, 2H), 7.83 (t, J=6.6 Hz, 1H), 8.20 (d, J=8.7 Hz, 2H).

Aufarbeitung

  1. extractionThe solution was extracted with ethyl acetate (2×100 mL)
  2. customThe organic solution was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-3c8a51594f714f52b5bdc5afff0a89b2
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040543B2

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