Acetonitrile → HCID 68971803, compound

HRID 1992594Notes

Reaction equation

HRID 1992594 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:11][CH2:12][CH2:13][CH2:14][OH:15])[C:5]([CH3:16])=[C:4]([CH3:17])[N:3]=1.[N-:18]=[N+:19]=[N-:20].[Na+].O.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].C(#N)C>CN(C=O)C.O>[CH3:17][C:4]1[N:3]2[N:18]=[N:19][N:20]=[C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:11][CH2:12][CH2:13][CH2:14][OH:15])[C:5]=1[CH3:16]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 33557Sodium AzideHCID 21585214Cerium trichloride heptahydrateHCID 21913176HCID 21913176, compound

Product 1

HCID 68971803HCID 68971803, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]propan-1-ol (12.4 g, 47.8 mmol), sodium azide (6.20 g, 95.5 mmol), and cerium (III) chloride heptahydrate (8.90 g, 23.9 mmol) in 9:1 acetonitrile:water (160 mL) was heated at reflux for 16 hours, then was allowed to cool to room temperature. DMF was added and the mixture was filtered. The filter cake was washed with DMF. The filtrate was concentrated under reduced pressure to give an orange solid that was triturated with ethyl acetate and isolated by filtration to yield 9.60 g of 3-[(5,6-dimethyl-8-nitrotetraazolo[1,5-α]pyridin-7-yl)amino]propan-1-ol as a yellow solid.

Workup

  1. temperatureat reflux for 16 hours
  2. filtrationthe mixture was filtered
  3. washThe filter cake was washed with DMF
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto give an orange solid
  6. customthat was triturated with ethyl acetate
  7. customisolated by filtration

Sources & evidence

ORD record
ord-610cac1b5ea544bcb5d6d6e4feb16078
Source dataset
uspto-grants-2010_01
Patent number
US07648997B2

Reaction notes

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