2-Thiophenecarboxaldehyde → HCID 13669814, compound

HRID 620761Notes

Reaction equation

HRID 620761 reaction equation
[O:1]=[C:2]([NH:16][C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([OH:21])=[O:20])[CH2:3][C:4]([NH:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])=[O:5].[S:26]1[CH:30]=[CH:29][CH:28]=[C:27]1[CH:31]=O>N1C=CC=CC=1>[O:5]=[C:4]([NH:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])[C:3](=[CH:31][C:27]1[S:26][CH:30]=[CH:29][CH:28]=1)[C:2]([NH:16][C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([OH:21])=[O:20])=[O:1]

Participants

4

Reactant 2

HCID 73642-ThiophenecarboxaldehydeHCID 130175852,2'-[(1,3-Dioxopropane-1,3-diyl)diazanediyl]dibenzoic acid

Product 1

HCID 13669814HCID 13669814, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2,2'-[(1,3-Dioxo-1,3-propanediyl)diimino]bisbenzoic acid (1.0 g, 2.92 mmol) and 2-thiophenealdehyde (0.49 g, 4.38 mmol) were heated under reflux in dry pyridine (8 ml) for 16 hours. After removing pyridine, the mixture was treated with water, made alkaline with 10% aqueous ammonia under ice cooling, and washed with ether. The aqueous layer was made acidic with 1N.HCl under ice cooling, and the precipitated crystals were collected on filter and washed with water. The resulting solid was purified by silica gel column chromatography and the effluent containing the desired compound was collected. After removing solvent, the residue was crystallized by treating water, collected by filtration, washed with water, and dried to give the title compound (0.730 g, yield, 57%), which was recrystallized from the mixed solvent of CH3OH--H2O to give the pale yellow crystals (0.602 g). m.p.: 213°-215° C.

Workup

  1. customAfter removing pyridine
  2. additionthe mixture was treated with water
  3. washwashed with ether
  4. customHCl under ice cooling, and the precipitated crystals were collected
  5. filtrationon filter
  6. washwashed with water
  7. customThe resulting solid was purified by silica gel column chromatography
  8. additionthe effluent containing the desired compound
  9. customwas collected
  10. customAfter removing solvent
  11. customthe residue was crystallized
  12. additionby treating water
  13. filtrationcollected by filtration
  14. washwashed with water
  15. customdried

Sources & evidence

ORD record
ord-7742d304aa2a4fe0a90e1198d0a38e23
Source dataset
uspto-grants-1989_04
Patent number
US04822791

Reaction notes

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