Toluene → HCID 53741675, Verbindung

HRID 279458Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 279458
Cl.N[CH2:3][CH2:4][SH:5].C1(C)C=CC=CC=1.C(N(CC)CC)C.[CH3:20][C:21]1[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][C:22]=1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31](=[N:34][O:35][CH3:36])[C:32]#[N:33]>O.O.C([O-])(=O)C.[Zn+2].C([O-])(=O)C.O>[CH3:36][O:35][N:34]=[C:31]([C:32]1[S:5][CH2:4][CH2:3][N:33]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[CH2:24][O:23][C:22]1[CH:37]=[C:38]([CH3:41])[CH:39]=[CH:40][C:21]=1[CH3:20]

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 8471TriethylamineHCID 9082Cysteamine HydrochlorideHCID 54390956HCID 54390956, Verbindung

Produkt 1

HCID 53741675HCID 53741675, VerbindungAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2724192Zinc acetate (USP)KatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

2-Aminoethanethiol hydrochloride (2.80 g, 24.6 mmol), zinc acetate dihydrate (600 mg, 2.7 mmol), toluene (12 ml) and triethylamine (3.12 g, 30.8 mmol) were added to 2-(2,5-dimethylphenoxymethyl)-α-methoxyiminophenylacetonitrile (6.00 g, 20.4 mmol), and the mixture was stirred under reflux for 14 hours. After completion of the reaction, water (100 ml) was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give 2-(2,5-dimethylphenoxymethyl)phenyl 2-thiazolin-2-yl ketone O-methyloxime (5.71 g, 79.0%) as crystals.

Aufarbeitung

  1. temperatureunder reflux for 14 hours
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-12ba8887ab8b4ad481f423354f700955
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06362212B1

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