Isopropyl iodide → 5-Chloro-2-isopropyl 4-nitrobenzotriazole

HRID 1733156Notes

Reaction equation

HRID 1733156 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]2[NH:6][N:7]=[N:8][C:4]=2[C:3]=1[N+:11]([O-:13])=[O:12].[CH:14](I)([CH3:16])[CH3:15]>C(#N)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]2=[N:6][N:7]([CH:14]([CH3:16])[CH3:15])[N:8]=[C:4]2[C:3]=1[N+:11]([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 6362Isopropyl iodideHCID 178526738HCID 178526738, compound

Product 1

HCID 203004105-Chloro-2-isopropyl 4-nitrobenzotriazoleYield 63%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a hot, stirred solution (50° C.) of 20.0 grams of 5-chloro-4-nitrobenzotriazole in 600 milliliters of acetonitrile is added 4.2 grams of sodium hydroxide pels and 20.0 grams of isopropyl iodide. The solution is then heated to reflux for 30 hours, filtered and the solvent removed by evaporation to yield an oil. The oil is extracted with concentrated hydrochloric acid (3×200 milliliters) and the resulting solid is collected, washed with water and air dried to yield 15.0 grams (63%) of crude 5-chloro-2-isopropyl 4-nitrobenzotriazole, m.p. 67°-70° C. The analytical sample is recrystallized from n-hexane and has a m.p. 75°-76° C.

Workup

  1. temperatureThe solution is then heated
  2. temperatureto reflux for 30 hours
  3. filtrationfiltered
  4. customthe solvent removed by evaporation
  5. customto yield an oil
  6. extractionThe oil is extracted with concentrated hydrochloric acid (3×200 milliliters)
  7. customthe resulting solid is collected
  8. washwashed with water and air
  9. customdried

Sources & evidence

ORD record
ord-413d8fb200dd4b2b940c6421661d3cf7
Source dataset
uspto-grants-1980_12
Patent number
US04240822

Reaction notes

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