Reaktion #95511

Reaktionsgleichung

hexahydro-2H-1,3-diazepin-2-thione

o-chlorobenzaldehyde

potassium cyanide

ethanol

→

desired product

2,3-Bis(o-chlorophenyl)-2,3,5,6,7,8-hexahydrothiazolo[3,2-a][1,3]diazepin-3-ol hydrochloride

Lösungsmittel

Water

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONA mixture of 22.6 ml
2. 2
   Sonstigethe water layer is decanted
3. 3
   workup.DISSOLUTIONthe oil dissolved in toluene
4. 4
   Waschenwashed with water
5. 5
   Sonstigedried
6. 6
   Einengenconcentrated to an oil
7. 7
   Sonstigegiving an oil
8. 8
   Sonstigeportion of this oil is reacted with 2.6 g
9. 9
   Sonstigegiving 1.4 g

Vorschrift

A mixture of 22.6 ml. of o-chlorobenzaldehyde, 8 g. of potassium cyanide and 100 ml. of 65% ethanol is refluxed for 2 hours and then refrigerated. Water (30 ml.) is added, refrigeration is continued, then the water layer is decanted and the oil dissolved in toluene, washed with water, dried and concentrated to an oil. The crude 2,2'-dichlorobenzoin is converted to the methanesulfonate ester as described in Example 1, giving an oil. A 14.6 g. portion of this oil is reacted with 2.6 g. of hexahydro-2H-1,3-diazepin-2-thione in 100 ml. of acetone as described in Example 13, giving 1.4 g. of the desired product, m.p. 224°-226° C.

Quelle