Sodium Hydroxide → HCID 69586325, compound

HRID 985099Notes

Reaction equation

HRID 985099 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][N:7]2[C:10]([CH3:14])=[C:11]([CH3:13])[N:12]=[C:6]2[C:5]=1[NH2:15])(=[O:3])[CH3:2].[S:16]1[CH:20]=[CH:19][C:18]([CH:21]=O)=[CH:17]1.[OH-].[Na+]>C(O)C>[NH2:15][C:5]1[C:6]2[N:7]([C:10]([CH3:14])=[C:11]([CH3:13])[N:12]=2)[CH:8]=[CH:9][C:4]=1[C:1](=[O:3])[CH:2]=[CH:21][C:18]1[CH:19]=[CH:20][S:16][CH:17]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 681353-ThiophenecarboxaldehydeHCID 21873921HCID 21873921, compound

Product 1

HCID 69586325HCID 69586325, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5 g of 7-acetyl-8-amino-2,3-dimethylimidazo[1,2-a]pyridine, 2.9 g of thiophene-3-carboxaldehyde, 1.6 g of sodium hydroxide and 100 ml of ethanol is stirred at room temperature for 3 days. It is then concentrated in vacuo to half the volume, poured onto 100 ml of saturated aqueous ammonium chloride solution and extracted three times with 100 ml of methylene chloride each time. The combined organic phases are washed with a little water, the solvent is stripped off in vacuo and the residue is stirred in ethyl ether. After filtering off and drying in vacuo, 4.6 g of the title compound are obtained.

Workup

  1. concentrationIt is then concentrated in vacuo to half the volume
  2. additionpoured onto 100 ml of saturated aqueous ammonium chloride solution
  3. extractionextracted three times with 100 ml of methylene chloride each time
  4. washThe combined organic phases are washed with a little water
  5. stirringthe residue is stirred in ethyl ether
  6. filtrationAfter filtering off
  7. dry with materialdrying in vacuo, 4.6 g of the title compound
  8. customare obtained

Sources & evidence

ORD record
ord-b317b0fd1f6746e9a8c2cf98298c5af8
Source dataset
uspto-grants-2005_03
Patent number
US06869949B2

Reaction notes

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