(4-Nitrophenyl)acetic acid → HCID 22594953, Verbindung

HRID 2221328Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2221328
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:12]([Br:13])=[CH:11][N:10]([CH3:14])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[N+:15]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25](O)=[O:26])=[CH:20][CH:19]=1)([O-:17])=[O:16].O.ON1C2C=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>C(Cl)(Cl)Cl.[Cl-].[Na+].O>[Br:13][C:12]1[C:8]([C:4]2[CH:3]=[C:2]([NH:1][C:25](=[O:26])[CH2:24][C:21]3[CH:20]=[CH:19][C:18]([N+:15]([O-:17])=[O:16])=[CH:23][CH:22]=3)[CH:7]=[CH:6][CH:5]=2)=[N:9][N:10]([CH3:14])[CH:11]=1

Komponenten

8

Edukt 5

HCID 4661(4-Nitrophenyl)acetic acidHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27353913-(4-Bromo-1-Methyl-1H-Pyrazol-3-Yl)AnilineHCID 27960291-Hydroxybenzotriazole hydrate

Produkt 1

HCID 22594953HCID 22594953, VerbindungAusbeute 18,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

A mixture of 3-(3-aminophenyl)-4-bromo-1-methylpyrazole (30 mg, 0.12 mmol), 4-nitrophenylacetic acid (22 mg, 0.12 mmol), 1-hydroxybenzotriazole hydrate (16 mg, 0.12 mmol) and 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (46 mg, 0.12 mmol) were dissolved in chloroform (1.5 ml). N,N-Diisopropylethylamine (0.02 ml, 0.13 mmol) was added and the mixture stirred at room temperature for 16 h. The reaction mixture was then poured into brine and the organic layer washed with further brine, dried over magnesium sulphate and then concentrated in vacuo. The crude product was purified by column chromatography (ethyl acetate-toluene, 1:1), giving the title compound (9 mg, 18%). Rf 0.19 (ethyl acetate-toluene, 1:1).

Aufarbeitung

  1. washthe organic layer washed with further brine
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by column chromatography (ethyl acetate-toluene, 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-19d4b8312e7442b086a76609574abc37
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07368539B2

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