Benzaldehyde → HCID 20528326, Verbindung

HRID 67235

Reaktionsgleichung

Reaktionsgleichung von HRID 67235
[C-]#N.[K+].C(=O)C1C=CC=CC=1.S1C=CC=C1[C:17]([C:25]([C:27]([OH:39])([C:34]1[S:35][CH:36]=[CH:37][CH:38]=1)C1C=CC=CC=1)=O)(O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20]C=1.[CH3:40][S:41](Cl)(=[O:43])=[O:42].[NH:45]1[CH2:51][CH2:50][CH2:49][CH2:48][NH:47][C:46]1=[S:52]>CC(C)=O.C(O)C>[CH3:40][S:41]([O:39][C:27]1([C:34]2[S:35][CH:36]=[CH:37][CH:38]=2)[N:47]2[CH2:48][CH2:49][CH2:50][CH2:51][N:45]=[C:46]2[S:52][CH:25]1[C:17]1[CH:18]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:43])=[O:42]

Komponenten

8

Edukt 5

HCID 240BenzaldehydeHCID 9032Potassium CyanideHCID 31297Methanesulfonyl chlorideHCID 7365891,3-Diazepane-2-thioneHCID 540020012-Thienyl-alpha-hydroxybenzyl ketone

Produkt 1

HCID 20528326HCID 20528326, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 9.2 ml. of thiophene-2-carboxyaldehyde, 8 g. of potassium cyanide and 10.1 ml. of benzaldehyde in 100 ml. of 65% ethanol is reacted as described in Example 20, giving 6.2 g. of 2-thienyl-α-hydroxybenzyl ketone. A 4.36 g. portion of this ketone is reacted with methanesulfonyl chloride as described in Example 20, giving 3.2 g. of the methanesulfonate ester. A 2.64 g. portion of this ester and 1.30 g. of hexahydro-2H-1,3-diazepine-2-thione in 100 ml. of acetone are allowed to stand 48 hours, the solid is collected, washed with ether and dried in vacuo, giving 2.8 g. of the desired product, m.p. 149°-151° C.

Aufarbeitung

  1. additionA mixture of 9.2 ml
  2. customgiving 6.2 g
  3. customgiving 3.2 g
  4. customthe solid is collected
  5. washwashed with ether
  6. customdried in vacuo
  7. customgiving 2.8 g

Quellen und Nachweise

ORD-Eintrag
ord-34472b1a55034bc2a3b0726c4608e611
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04344954

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