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Hydroxylamine → HCID 67217531, Verbindung

HRID 1505281
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1505281
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:12])[N:7]=[C:8]([CH:10]=O)[CH:9]=1)=[O:4].[NH2:13][OH:14].ClN1C(=O)CCC1=O.[Cl:23][C:24]1[CH:29]=[C:28]([C:30]([C:32]([F:35])([F:34])[F:33])=[CH2:31])[CH:27]=[C:26]([Cl:36])[CH:25]=1>C(O)C.CN(C)C=O.C(N(CC)CC)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:12])[N:7]=[C:8]([C:10]2[CH2:31][C:30]([C:28]3[CH:29]=[C:24]([Cl:23])[CH:25]=[C:26]([Cl:36])[CH:27]=3)([C:32]([F:33])([F:34])[F:35])[O:14][N:13]=2)[CH:9]=1)=[O:4]
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Komponenten

8

Edukt 4

HCID 787HydroxylamineHCID 31398ChlorosuccinimideHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 58498000Methyl 3-formyl-1-methyl-1H-pyrazole-5-carboxylate

Produkt 1

HCID 67217531HCID 67217531, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702
Ethanol
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel2×
HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of 5-Formyl-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (210 mg) in ethanol (10 mL), was added aqueous NH2OH (50% in water, 0.10 mL). The solution was stirred at room temperature for 4 hours then was concentrated to give a white solid which was then dissolved in dimethylformamide (4 mL). To this solution was added N-chlorosuccinimide (180 mg). The solution was stirred at room temperature for 4 hours. This solution was slowly added to a solution of 1,3-Dichloro-5-(1-trifluoromethyl-vinyl)-benzene (750 mg) (prepared according to WO 2005/085216) in dimethylformamide (6 mL). When the addition was completed, triethylamine (0.2 mL) was added. The solution was stirred at room temperature for 4 hours then the reaction was then quenched by addition of water. After extraction with diethyl ether, the organic phase was separated, dried over magnesium sulfate and concentrated to give an orange oil. The residue was purified by chromatography over silica (heptane/diethyl ether; 1/0 to 7/3) to give 300 mg of 5-[5-(3,5-Dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester as a white solid. 1H-NMR (CDCl3, 400 MHz): 7.48 (m, 2H), 7.39-7.38 (m, 1H), 7.23 (s, 1H), 4.17 (s, 3H), 4.14 (d, 1H), 3.89 (s, 3H), 3.75 (d, 1H).

Aufarbeitung

  1. concentrationthen was concentrated
  2. customto give a white solid which
  3. stirringThe solution was stirred at room temperature for 4 hours
  4. additionWhen the addition
  5. stirringThe solution was stirred at room temperature for 4 hours
  6. customthe reaction was then quenched by addition of water
  7. extractionAfter extraction with diethyl ether
  8. customthe organic phase was separated
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated
  11. customto give an orange oil
  12. customThe residue was purified by chromatography over silica (heptane/diethyl ether; 1/0 to 7/3)

Quellen und Nachweise

ORD-Eintrag
ord-a4fa89458aa5455f863de37cecd189c2
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09216973B2

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