Lactonitrile → HCID 178484853, Verbindung

HRID 25667

Reaktionsgleichung

Reaktionsgleichung von HRID 25667
Br[CH2:2][CH2:3][CH2:4][O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([N:12]([CH3:26])[S:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:8][CH2:7]1.CC(O)[C:29]#[N:30].N12CCCN=C1CCCCC2>C(#N)C>[C:29]([CH2:2][CH2:3][CH2:4][O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([N:12]([CH3:26])[S:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:8][CH2:7]1)#[N:30]

Komponenten

5

Edukt 3

HCID 6572Lactonitrile2×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 178484846HCID 178484846, Verbindung

Produkt 1

HCID 178484853HCID 178484853, VerbindungAusbeute 41,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel3×

Versuchsvorschrift

To 1.0 g (2.18 mmol) trans-N-[4-(3-Bromo-propoxy)-cyclohexyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide in 10 ml acetonitrile was added 0.29 ml (3.1 mmol) acetocyanhydrine in 5 ml acetonitrile and 0.37 ml (2.5 mmol) 1,8-Diazabicyclo-(5,4,0)-undec-7-ene in 5 ml acetonitrile. The solution was stirred at RT over night. An additonal amount of acetocyanhydrine and 1,8-Diazabicyclo-(5,4,0)-undec-7-ene were added and the solution stirred at 50° C. for 6 h. The mixture was concentrated and dissolved in water/ether. The organic phase was washed with brine, dried over Na2SO4 and was evaporated to give 366 mg (41%) trans-N-[4-(3-Cyano-propoxy)-cyclohexyl]-N-methyl-4-trifluoromethyl-benzenesulfonamide as light yellow oil, MS: 404 (M).

Aufarbeitung

  1. stirringthe solution stirred at 50° C. for 6 h
  2. concentrationThe mixture was concentrated
  3. dissolutiondissolved in water/ether
  4. washThe organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. customwas evaporated

Quellen und Nachweise

ORD-Eintrag
ord-19a319e7fabe4c418e92433f29cf6727
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858651B2

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