Chloroacetonitrile → 3-Amino-4,5,6,7-tetrahydrobenzo[1,2-b]selenophene-2-carbonitrile

HRID 1097226

Reaktionsgleichung

Reaktionsgleichung von HRID 1097226
[Se-2:1].[Na+].[Na+].Cl[C:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=1[C:11]#[N:12].Cl[CH2:14][C:15]#[N:16].C[O-].[Na+]>CN(C=O)C.CO.O>[NH2:12][C:11]1[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:5]=2[Se:1][C:14]=1[C:15]#[N:16]

Komponenten

8

Edukt 4

HCID 7856ChloroacetonitrileHCID 73973Sodium selenideHCID 10942334Sodium MethoxideHCID 498409392-Chlorocyclohex-1-ene-1-carbonitrile

Produkt 1

HCID 595472123-Amino-4,5,6,7-tetrahydrobenzo[1,2-b]selenophene-2-carbonitrileAusbeute 57,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a suspension of sodium selenide (2.35 g, 18.65 mmol, prepared from 1.5 g of selenium as described above) in DMF (18 mL) was added a solution of 2-chlorocyclohex-1-enecarbonitrile (2.63 g, 18.65 mmol) in DMF (9 mL) at rt for 5 min and stirred the mixture at 60° C. for 45 min. Then chloroacetonitrile (1.18 mL, 18.65 mmol) was added dropwise to the reaction mixture and again stirred at 60° C. for 3 h. Then, a solution of sodium methoxide (1.0 g, 18.65 mmol) in dry methanol (18 mL) was added dropwise and stirring was continued for 2 h at the same temperature. The mixture was allowed to room temperature (rt) and poured into cold water and stirred for 30 min. The precipitated solid was filtered and washed with water to give the product as a dark brown color solid (2.4 g, 57%), mp 86-88° C. 1H NMR (400 MHz, CDCl3): δ 4.39 (2H, br s, —NH2), 2.73-2.74 (2H, m, H-7), 2.28-2.29 (2H, m, H-4), 1.83-1.84 (4H, m, H-5,6).

Aufarbeitung

  1. stirringagain stirred at 60° C. for 3 h
  2. stirringstirring
  3. waitwas continued for 2 h at the same temperature
  4. customwas allowed to room temperature
  5. custom(rt)
  6. stirringstirred for 30 min
  7. filtrationThe precipitated solid was filtered
  8. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-9d944fe511184241983645703a471151
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143237B2

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