Chloroacetonitrile → HCID 14349018, Verbindung

HRID 346059Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 346059
C(O)(=O)C(O)=O.[F:7][C:8]([F:28])([F:27])[C:9]1[CH:26]=[CH:25][C:12]([O:13][CH:14]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[CH2:18][CH2:17][NH:16][CH2:15]2)=[CH:11][CH:10]=1.Cl[CH2:30][C:31]#[N:32].C(=O)(O)[O-].[Na+]>CN(C=O)C>[C:31]([CH2:30][N:16]1[CH2:15][CH:14]([O:13][C:12]2[CH:25]=[CH:26][C:9]([C:8]([F:7])([F:27])[F:28])=[CH:10][CH:11]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH2:18][CH2:17]1)#[N:32]

Komponenten

5

Edukt 3

HCID 7856ChloroacetonitrileHCID 516892Sodium BicarbonateHCID 14348987HCID 14348987, Verbindung

Produkt 1

HCID 14349018HCID 14349018, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 2,3,4,5-tetrahydro-1-(p-trifluoromethylphenoxy)-3-benzazepine of Example 1 (16 g, 0.052 mole), chloroacetonitrile (8 g, 0.10 mole) and sodium bicarbonate (17 g, 0.20 mole) in DMF (125 ml) was warmed at 70° C. for 2.5 hours. The mixture was concentrated to an oil which was stirred with water and extracted with ethyl acetate. The organic extracts were washed twice with water and dried (saturated NaCl, anhydrous MgSO4). After filtering, the solvent was evaporated to an oil (18 g) which solidified upon triturating with petroleum ether to a solid (16.5 g, 92%, m.p. 125°-129° C. A sample was recrystallized from the hexanes to yield 3-cyanomethyl-2,3,4,5-tetrahydro-1-(p-trifluoromethylphenoxy)-3-benzazepine, m.p. 134°-135° C.

Aufarbeitung

  1. concentrationThe mixture was concentrated to an oil which
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts were washed twice with water
  4. dry with materialdried (saturated NaCl, anhydrous MgSO4)
  5. filtrationAfter filtering
  6. customthe solvent was evaporated to an oil (18 g) which
  7. customupon triturating with petroleum ether to a solid (16.5 g, 92%, m.p. 125°-129° C
  8. customA sample was recrystallized from the hexanes

Quellen und Nachweise

ORD-Eintrag
ord-52cb4a6dfa534fbb8aa437c6f7116a8b
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05059688

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