Benzaldehyde → HCID 20528326, compound

HRID 67235

Reaction equation

HRID 67235 reaction equation
[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]

Participants

8

Reactant 5

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

Product 1

HCID 20528326HCID 20528326, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-34472b1a55034bc2a3b0726c4608e611
Source dataset
uspto-grants-1982_08
Patent number
US04344954

Linked notes

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