Dimethylformamide → HCID 11499770, compound

HRID 1823324Notes

Reaction equation

HRID 1823324 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([NH:11][CH2:12][CH:13]([CH3:15])[CH3:14])[CH:5]=[C:4]([CH3:16])[N:3]=1.[N-:17]=[N+:18]=[N-:19].[Na+].CN(C)C=O>O>[CH3:14][CH:13]([CH3:15])[CH2:12][NH:11][C:6]1[CH:5]=[C:4]([CH3:16])[N:3]2[N:17]=[N:18][N:19]=[C:2]2[C:7]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 115215932-Chloro-N-(2-methylpropyl)-6-methyl-3-nitropyridin-4-amine

Product 1

HCID 11499770HCID 11499770, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Under a nitrogen atmosphere, a mixture of 2-chloro-N-(2-methylpropyl)-6-methyl-3-nitropyridin-4-amine (10.0 g, 41.0 mmol), sodium azide (2.67 g, 41.0 mmol), and anhydrous N,N-dimethylformamide (200 mL) was heated at 60° C. After 5 hours, the dark green solution was allowed to cool to room temperature, poured slowly into water (2 L), and stirred for fifteen minutes. A green precipitate formed, which was filtered and washed with water to yield 9.37 g of N-(2-methylpropyl)-5-methyl-8-nitrotetraazolo[1,5-a]pyridin-7-amine as a light green solid, m.p. 185–187° C.

Workup

  1. temperatureto cool to room temperature
  2. customA green precipitate formed
  3. filtrationwhich was filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-1f2c8959cc8a4ac2baeec09522a74085
Source dataset
uspto-grants-2006_05
Patent number
US07038053B2

Reaction notes

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