Benzaldehyde, 4-(2-hydroxyethoxy)- → HCID 178492971, compound

HRID 2218427Notes

Reaction equation

HRID 2218427 reaction equation
[Cl:1][C:2]1[C:3]([O:10][CH3:11])=[C:4]([NH2:9])[C:5]([NH2:8])=[N:6][CH:7]=1.[OH:12][CH2:13][CH2:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1>CN(C=O)C.O.O.O.O.O.O.[Fe](Cl)(Cl)Cl>[Cl:1][C:2]1[C:3]([O:10][CH3:11])=[C:4]2[N:9]=[C:20]([C:19]3[CH:22]=[CH:23][C:16]([O:15][CH2:14][CH2:13][OH:12])=[CH:17][CH:18]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 89178Benzaldehyde, 4-(2-hydroxyethoxy)-HCID 57482673HCID 57482673, compound

Product 1

HCID 178492971HCID 178492971, compound

Reagents, catalysts & solvents 2

HCID 16211236Trichloroiron;hexahydrateCatalystHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
110 °C

Procedure

5-Chloro-4-methoxypyridin-2,3-diamine (0.498 g, 2.9 mmol) was dissolved in DMF (7 ml). Iron(III)chloride hexahydrate (0.06 g, 0.2 mmol) was added and the mixture heated to is 80° C. 4-(2-Hydroxyethoxy)benzaldehyde (0.48 g, 2.9 mmol) dissolved in DMF (4 ml) was added dropwise, and the reaction mixture was heated at 110° C. for 11 h with air bubbling through the solution. The solvent was removed by evaporation, the solid residue was dissolved in warm methanol and filtered through a short plug of silica gel. Following evaporation and recrystallization (methanol), the title compound was isolated (0.26 g, 28%).

Workup

  1. temperaturethe mixture heated
  2. customto is 80° C
  3. additionwas added dropwise
  4. custombubbling through the solution
  5. customThe solvent was removed by evaporation
  6. dissolutionthe solid residue was dissolved in warm methanol
  7. filtrationfiltered through a short plug of silica gel
  8. customevaporation and recrystallization (methanol)

Sources & evidence

ORD record
ord-0ffe4ec3207f43de88181c4a0bb8349b
Source dataset
uspto-grants-2008_08
Patent number
US07410966B2

Reaction notes

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