Diisopropylethylamine → N-(sec-butylsulfonyl)-2,4,5-trifluorobenzamide

HRID 2048081Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2048081
Cl.CN(C)CCCN=C=NCC.C(N(C(C)C)C(C)C)C.[F:22][C:23]1[CH:31]=[C:30]([F:32])[C:29]([F:33])=[CH:28][C:24]=1[C:25]([OH:27])=O.[CH3:34][CH:35]([S:38]([NH2:41])(=[O:40])=[O:39])[CH2:36][CH3:37]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH:35]([S:38]([NH:41][C:25](=[O:27])[C:24]1[CH:28]=[C:29]([F:33])[C:30]([F:32])=[CH:31][C:23]=1[F:22])(=[O:40])=[O:39])([CH2:36][CH3:37])[CH3:34]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 5211702,4,5-Trifluorobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 20482438Butane-2-sulfonamide

Produkt 1

HCID 58042392N-(sec-butylsulfonyl)-2,4,5-trifluorobenzamideAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (0.41 g, 2.1 mmol), 4-dimethylaminopyridine (0.26 g, 2.1 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.9 mL, 4.2 mmol) were added to a solution of 2,4,5-trifluorobenzoic acid (0.25 g, 1.4 mmol) in DCM. After 10 minutes butane-2-sulfonamide (Preparation 29, 0.29 g, 2.1 mmol) was added and the reaction was left at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and the residue purified by preparative HPLC to yield the title compound as a white solid (0.19 g, 31% yield):

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-e254bd20fc5b4f30be7e04f2817fb323
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592629B2

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