Water → HCID 57752451, Verbindung

HRID 225416

Reaktionsgleichung

Reaktionsgleichung von HRID 225416
Cl.[CH2:2]([O:5][NH2:6])[CH:3]=[CH2:4].C(N(CC)CC)C.[CH2:14]([S:21][C:22]1[N:26]([CH3:27])[N:25]=[C:24]([Cl:28])[C:23]=1[C:29](Cl)=[O:30])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>O1CCCC1>[CH2:14]([S:21][C:22]1[N:26]([CH3:27])[N:25]=[C:24]([Cl:28])[C:23]=1[C:29]([NH:6][O:5][CH2:2][CH:3]=[CH2:4])=[O:30])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 3084724O-Allylhydroxylamine hydrochlorideHCID 87489965HCID 87489965, Verbindung

Produkt 1

HCID 57752451HCID 57752451, VerbindungAusbeute 101,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

In a suspension of allyloxyamine hydrochloride (2.3 g, 21 mmol) in tetrahydrofuran (20 ml), 2.9 g (29 mmol) of triethylamine was added at 0° C., stirred at room temperature for 5 minutes and then a solution of 5-benzylthio-3-chloro-1-methylpyrazole-4-carboxylic acid chloride (2.1 g, 7.0 mmol) in tetrahydrofuran (10 ml) was added dropwise. After stirring at room temperature for 1 hour, water (100 ml) was added and extracted with ethyl acetate. The resulting ethyl acetate solution was washed with saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate and the solvent was distilled off to obtain the desired product (2.4 g). Oily substance. Proton nuclear magnetic resonance chemical shift values δ (ppm) (in CDCl3) 3.45 (s, 3H), 4.11 (s, 2H), 4.53 (d, J=6.3 Hz, 2H), 5.34-5.45 (m, 2H), 6.00-6.13 (m, 1H), 7.03-7.06 (m, 2H), 7.24-7.28 (m, 3H), 9.14 (brs, 1H).

Aufarbeitung

  1. additionwas added at 0° C.
  2. stirringAfter stirring at room temperature for 1 hour
  3. extractionextracted with ethyl acetate
  4. washThe resulting ethyl acetate solution was washed with saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-013e9902440b4492b18d78aae8d5741e
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557067B2

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