Benzaldehyde → N-benzal-6-(methylthio)pyridine-3-amine

HRID 1523273Notes

Reaction equation

HRID 1523273 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][N:4]=1.[CH:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4].O1CCCC1>[CH:10](=[N:9][C:6]1[CH:5]=[N:4][C:3]([S:2][CH3:1])=[CH:8][CH:7]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 10340Sodium CarbonateHCID 102611796-(Methylsulfanyl)pyridin-3-amine

Product 1

HCID 89962644N-benzal-6-(methylthio)pyridine-3-amine

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-(methylthio)-5-aminopyridine (1 g, 7 mmol), benzaldehyde (0.76 g, 7 mmol), tetraisopropyl titanate (3 mL) and tetrahydrofuran (25 mL) were mixed and stirred to react at 70° C. for 24 hours. Saturated sodium carbonate solution was added into the reaction mixture, and the mixture was extracted with ethyl acetate for three times. The combined organic phase was dried with anhydrous sodium sulfate, filtered and concentrated to yield the residual (1.72 g), which was directly used in the next reaction step without purification.

Workup

  1. customto react at 70° C. for 24 hours
  2. extractionthe mixture was extracted with ethyl acetate for three times
  3. dry with materialThe combined organic phase was dried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield the residual (1.72 g), which
  7. customwas directly used in the next reaction step without purification

Sources & evidence

ORD record
ord-8de93fd91f2344f3bfd0aaed68e6a7ec
Source dataset
uspto-grants-2015_07
Patent number
US09079876B2

Reaction notes

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