Dimethylformamide → 2-Chlorocyclohex-1-ene-1-carbonitrile

HRID 1422984

Reaktionsgleichung

Reaktionsgleichung von HRID 1422984
O=P(Cl)(Cl)Cl.C[N:7]([CH:9]=O)C.[C:11]1(=O)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[ClH:18].NO>O>[Cl:18][C:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=1[C:9]#[N:7]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 7967CyclohexanoneHCID 24813Phosphorus oxychlorideHCID 443297Hydroxyamine hydrochloride

Produkt 1

HCID 498409392-Chlorocyclohex-1-ene-1-carbonitrileAusbeute 60,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a stirring solution of POCl3 (15.20 mL, 163 mmol) at 0° C. was added DMF (13.40 mL, 173 mmol) drop-wise. Monitoring internal temperature, cyclohexanone (10.60 mL, 102 mmol) was slowly added, keeping the temperature between 35 and 40° C. Upon complete addition, the reaction was heated to 50° C. and hydroxylamine hydrochloride (40 g, 576 mmol) was added in eight portions, cooling when necessary to control the exothermic reaction. Upon completing this addition, ice was added to the reaction, followed by water (400 mL), and the mixture resumed stirring for 1 h. Filtration afforded the desired product as a brown solid (8.8 g). Some substrates may require an aqueous work-up/extraction procedure if water solubility is too high. EtOAc is generally a good solvent for this extraction. MS: No signal. 1H NMR (400 MHz, CDCl3 δ ppm 2.47-2.36 (m, 2H), 2.34-2.25 (m, 2H), 1.78-1.67 (m, 1H), 1.67-1.58 (m, 1H).

Aufarbeitung

  1. customthe temperature between 35 and 40° C
  2. additionUpon complete addition
  3. temperaturecooling when necessary
  4. customthe exothermic reaction
  5. additionthis addition, ice
  6. additionwas added to the reaction
  7. filtrationFiltration

Quellen und Nachweise

ORD-Eintrag
ord-33a83ba0f6104eacb346ab6c845a3bad
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927555B2

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