Benzaldehyde → HCID 54473566, compound

HRID 862114Notes

Reaction equation

HRID 862114 reaction equation
[CH2:1]([N:3]([CH2:15][CH3:16])[C:4]([C@@H:6]1[C@H:11]2[CH2:12][CH2:13][N:8]([CH2:9][C:10]2=[O:14])[CH2:7]1)=[O:5])[CH3:2].[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH-].[Na+]>CCO>[CH2:15]([N:3]([CH2:1][CH3:2])[C:4]([C@@H:6]1[C@H:11]2[CH2:12][CH2:13][N:8]([C:9](=[CH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:10]2=[O:14])[CH2:7]1)=[O:5])[CH3:16]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 22882067HCID 22882067, compound

Product 1

HCID 54473566HCID 54473566, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 13 (34.6 g, 154 mmole), benzaldehyde (17.4 g, 164 mmole) and NaOH (6.5 g, 164 mmole) in EtOH (400 ml) was refluxed for 3 hours. After cooling the reaction mixture to room temperature, the resulting yellow crystal was collected by filtration and washed with cold EtOH and dried in vacuo to give 14 (38.4 g, 128 mmole). The filtrate was concentrated under reduced pressure to give a second crop (3.3 g, 11 mmole) (total 41.7 g, 139 mmole, 90%).

Workup

  1. temperaturewas refluxed for 3 hours
  2. filtrationthe resulting yellow crystal was collected by filtration
  3. washwashed with cold EtOH
  4. customdried in vacuo

Sources & evidence

ORD record
ord-81bf6efd0c514146aff66f249742fbfd
Source dataset
uspto-grants-1998_02
Patent number
US05716965

Reaction notes

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