Benzaldehyde → HCID 86694680, compound

HRID 1523267Notes

Reaction equation

HRID 1523267 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([NH2:9])=[N:7][CH:8]=1.[CH:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>O1CCCC1>[CH:10](=[N:9][C:6]1[CH:5]=[CH:4][C:3]([S:2][CH3:1])=[CH:8][N:7]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 962WaterHCID 151797975-(Methylsulfanyl)pyridin-2-amine

Product 1

HCID 86694680HCID 86694680, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(methylthio)-2-aminopyridine (185 g) was dissolved in 2 L tetrahydrofuran, and then 500 mL titanate tetraisopropyl and benzaldehyde (155 g) were added. The reaction mixture was heated for reflux overnight, then cooled to room temperature, and 10 L water was added. The reaction mixture was extracted with ethyl acetate, the organic phase was washed with saturated NaCl solution, and dried with anhydrous sodium sulfate. After filtration, the residual solution was removed under reduced pressure to obtain the target compound (200 g).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperaturefor reflux overnight
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washthe organic phase was washed with saturated NaCl solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. customthe residual solution was removed under reduced pressure

Sources & evidence

ORD record
ord-be3fd80743bc4073b575dd69391781f0
Source dataset
uspto-grants-2015_07
Patent number
US09079876B2

Reaction notes

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