N,N-Dimethylaniline → 12-Chloro-7-thia-9,11-diazatricyclo(6.4.0.0,2,6)dodeca-1(12),2(6),8,10-tetraene

HRID 22786

Reaktionsgleichung

Reaktionsgleichung von HRID 22786
[N:1]1[C:6]2[S:7][C:8]3[CH2:13][CH2:12][CH2:11]C[C:9]=3[C:5]=2[C:4](=O)[NH:3][CH:2]=1.CN(C)C1C=CC=CC=1.O=P(Cl)(Cl)[Cl:26]>>[Cl:26][C:4]1[C:5]2[C:9]3[CH2:11][CH2:12][CH2:13][C:8]=3[S:7][C:6]=2[N:1]=[CH:2][N:3]=1

Komponenten

4

Edukt 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 986145,6,7,8-Tetrahydro(1)benzothieno(2,3-D)pyrimidin-4(3H)-one

Produkt 1

HCID 78981712-Chloro-7-thia-9,11-diazatricyclo(6.4.0.0,2,6)dodeca-1(12),2(6),8,10-tetraene

Versuchsvorschrift

To 10.56 g 5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3H)-one (0.51 mol) and 10 mL dimethylaniline was added, in one portion, 50 mL POCl3. The mixture was heated to reflux for 5 h under argon, cooled and the excess POCl3 was removed by concentration in vacuo. The residue was poured into 200 g ice and neutralized with satd Na2CO3. The resulting blue-gray gum was filtered, washed with water and crystallized from ethanol to give 7.03 g (0.031 mol) of product.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 5 h under argon
  3. temperaturecooled
  4. customthe excess POCl3 was removed by concentration in vacuo
  5. additionThe residue was poured into 200 g ice and neutralized with satd Na2CO3
  6. filtrationThe resulting blue-gray gum was filtered
  7. washwashed with water
  8. customcrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-f8d24aee8efc4d0395001177f0ee1e21
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06849638B2

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