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2-(Trifluoromethyl)benzoic acid → HCID 58792452, Verbindung

HRID 1359944
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1359944
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O.[CH3:14][C:15]([CH3:26])([CH3:25])[C:16]#[C:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH2:24].C(N(CC)C(C)C)(C)C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(#N)C.C(OCC)(=O)C.O>[CH3:14][C:15]([CH3:26])([CH3:25])[C:16]#[C:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH:24][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=1[C:2]([F:1])([F:13])[F:12]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 98992-(Trifluoromethyl)benzoic acidHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 140666562-(3,3-Dimethylbut-1-yn-1-yl)aniline

Produkt 1

HCID 58792452HCID 58792452, VerbindungAusbeute 38,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342
Acetonitrile
Lösungsmittel
HCID 22728543Water ethylacetateLösungsmittel

Versuchsvorschrift

190 mg (1.0 mmol) of 2-trifluoromethylbenzoic acid, 178 mg (0.83 mmol) of 2-(3,3-dimethyl-but-1-ynyl)phenylamine, 215 mg (1.67 mmol) of N,N-diisopropylethylamine and 583 mg (1.25 mmol) of PyBrOP in 8 ml of acetonitrile were stirred at room temperature for 4 days. 10 ml of ethyl acetate/water 1:1 were added to the mixture and the organic phase was separated off and washed with 10 ml of saturated ammonium chloride solution and subsequently with 10 ml of water. Separation, concentration and drying of the organic phase gave 950 mg of crude product. Column-chromatographic purification on silica gel 60 (petroleum ether/ethyl acetate 10:1→ethyl acetate) gave 110 mg of N-[2-(3,3-dimethylbut-1-ynyl)phenyl]-2-trifluoromethylbenzamide [logP (pH 2.3)=4.55].

Aufarbeitung

  1. customthe organic phase was separated off
  2. washwashed with 10 ml of saturated ammonium chloride solution and subsequently with 10 ml of water
  3. customSeparation, concentration
  4. customdrying of the organic phase
  5. customgave 950 mg of crude product
  6. customColumn-chromatographic purification on silica gel 60 (petroleum ether/ethyl acetate 10:1→ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-bac27973fdab406487443dc0bc1a1514
Quelldatensatz
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07879760B2

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