Chloride → 7-Phenylazepan-2-one

HRID 263483Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 263483
[C:1]1([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]2=[N:13]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.C1(C)C=CC(S(Cl)(=O)=[O:28])=CC=1.[Cl-]>O>[C:1]1([CH:7]2[NH:13][C:8](=[O:28])[CH2:9][CH2:10][CH2:11][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 312ChlorideHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 2758632-Phenylcyclohex-anone oxime

Produkt 1

HCID 105595527-Phenylazepan-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a 250 ml round-bottomed flask equipped with N2 inlet were added 7.33 g (38.8 mmol) 2-phenylcyclohexanone oxime (Chem. Ber., 55, 3664 (1922)) and 25 ml pyridine. The solution was cooled to 0° C., and 9.61 g (50.4 mmol) p-toluenesulfonyl chloride was added. The reaction was allowed to stir overnight as the ice melted, and then poured into water. Excess chloride was skimmed off the surface, and the reaction mixture was stirred at pH 4 for 3 hours. The precipitate was filtered, washed with water, and dried to a solid, 4.65 g (55%), mp 135°-137° C. (J. Am. Chem. Soc., 82, 4671 (1960) gives mp 139°-141° C.).

Aufarbeitung

  1. customTo a 250 ml round-bottomed flask equipped with N2 inlet
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried to a solid, 4.65 g (55%), mp 135°-137° C. (J. Am. Chem. Soc., 82, 4671 (1960) gives mp 139°-141° C.)

Quellen und Nachweise

ORD-Eintrag
ord-63666642e3534e789eac5e0c6485670b
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05643904

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