Tert-Butyl nitrite → HCID 14651251, compound

HRID 2396942Notes

Reaction equation

HRID 2396942 reaction equation
N(OC(C)(C)C)=O.[F:8][C:9]1[C:15]([CH3:16])=[C:14]([F:17])[C:13]([F:18])=[C:12]([CH3:19])[C:10]=1N>CN(C)C=O>[F:18][C:13]1[C:14]([F:17])=[C:15]([CH3:16])[C:9]([F:8])=[CH:10][C:12]=1[CH3:19]

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 23359007HCID 23359007, compound

Product 1

HCID 14651251HCID 14651251, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of t-butyl nitrite (4.56 g) in anhydrous dimethylformamide (26.5 ml) is stirred with heating at 50°-52° C. and thereto a solution of 2,4,5-trifluoro-3,6-dimethylaniline (4.24 g) in anhydrous dimethylformamide (40 ml) is added dropwise at 50°-52° C. over a period of 30 minutes. The mixture is further stirred at the same temperature for 30 minutes. After cooling, the mixture is poured into ice-water, extracted with diethyl ether, and the extract is washed with water, and then with diluted hydrochloric acid and dried. The diethyl ether is distilled off under atomospheric pressure and the residue is concentrated and distilled under atomospheric pressure to give 2,3,5-trifluoro-4-methyltoluene (1.9 g), as yellow oil, b.p. 120°-125° C.

Workup

  1. temperaturewith heating at 50°-52° C.
  2. temperatureAfter cooling
  3. extractionextracted with diethyl ether
  4. washthe extract is washed with water
  5. dry with materialwith diluted hydrochloric acid and dried
  6. distillationThe diethyl ether is distilled off under atomospheric pressure
  7. concentrationthe residue is concentrated
  8. distillationdistilled under atomospheric pressure

Sources & evidence

ORD record
ord-2fe7851eed53492289f295ae1593c35e
Source dataset
uspto-grants-1996_02
Patent number
US05495020

Reaction notes

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