Acetonitrile → HCID 57447078, compound

HRID 2366701Notes

Reaction equation

HRID 2366701 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:5]([CH3:20])=[C:4]([CH3:21])[N:3]=1.[N-:22]=[N+:23]=[N-:24].[Na+].O.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].C(#N)C>O>[CH3:21][C:4]1[N:3]2[N:22]=[N:23][N:24]=[C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:5]=1[CH3:20]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 33557Sodium AzideHCID 21585214Cerium trichloride heptahydrateHCID 57455392Ethyl 4-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]butyrate

Product 1

HCID 57447078HCID 57447078, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under a nitrogen atmosphere, a mixture of ethyl 4-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]butanoate (21.5 g, 68 mmol), sodium azide (8.90 g, 136 mmol), cerium(III) chloride heptahydrate (12.7 g, 34 mmol), and 9:1 acetonitrile:water (250 mL) was heated overnight at reflux. The hot reaction mixture was filtered, and the filter cake was washed with acetonitrile. The filtrate was concentrated under reduced pressure, and the residue was triturated with ethyl acetate:hexanes and isolated by filtration to provide 21.5 g of ethyl 4-[(5,6-dimethyl-8-nitrotetraazolo[1,5-a]pyridin-7-yl)amino]butanoate.

Workup

  1. temperatureat reflux
  2. filtrationThe hot reaction mixture was filtered
  3. washthe filter cake was washed with acetonitrile
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was triturated with ethyl acetate
  6. customhexanes and isolated by filtration

Sources & evidence

ORD record
ord-bcf075628bd64107abb81015c5d1c3ea
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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