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

HRID 67233

Reaktionsgleichung

Reaktionsgleichung von HRID 67233
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C-]#N.[K+].[CH2:13](O)[CH3:14].[NH:16]1[CH2:22][CH2:21][CH2:20][CH2:19][NH:18][C:17]1=[S:23]>CC(C)=O.O>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:6][CH:7]=[CH:8][C:13]=1[CH:14]1[S:23][C:17]2=[N:18][CH2:19][CH2:20][CH2:21][CH2:22][N:16]2[C:4]1([C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[Cl:1])[OH:5]

Komponenten

7

Edukt 4

HCID 702EthanolHCID 69962-ChlorobenzaldehydeHCID 9032Potassium CyanideHCID 7365891,3-Diazepane-2-thione

Produkt 1

HCID 205283212,3-Bis(o-chlorophenyl)-2,3,5,6,7,8-hexahydrothiazolo[3,2-a][1,3]diazepin-3-ol hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. additionA mixture of 22.6 ml
  2. customthe water layer is decanted
  3. dissolutionthe oil dissolved in toluene
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated to an oil
  7. customgiving an oil
  8. customportion of this oil is reacted with 2.6 g
  9. customgiving 1.4 g

Quellen und Nachweise

ORD-Eintrag
ord-cbe95206ec474485bf42dd91a942cc71
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04344954

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