Nitrogen → HCID 178437748, compound

HRID 2259480Notes

Reaction equation

HRID 2259480 reaction equation
[CH2:1]([Li])CCC.N#N.C(NC(C)C)(C)C.[NH:15]1[CH:19]=[N:18][C:17]([CH2:20][C:21]2([CH:28]=[CH:27][CH:26]=[CH:25][CH2:24]2)[C:22]#[N:23])=[N:16]1.CI>O1CCCC1>[NH:15]1[CH:19]=[N:18][C:17]([CH:20]([C:21]2([CH:24]=[CH:25][CH:26]=[CH:27][CH2:28]2)[C:22]#[N:23])[CH3:1])=[N:16]1

Participants

7

Reactant 5

HCID 947NitrogenHCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 178418339ButyllithiumHCID 178509426HCID 178509426, compound

Product 1

HCID 178437748HCID 178437748, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of n-butyl lithium (25 mL of 2.1M reagent in hexane, 0.0525 mole) is added dropwise in an N2 atmosphere to a solution of di-isopropylamine (5.6 g) in tetrahydrofuran (100 mL) which is maintained at -20°. This cold solution is then added dropwise to a solution of 4-[1-(1,2,4-triazolylmethyl)benzonitrile (9.10 g) in tetrahydrofuran (250 mL) which is maintained at -50° during addition and for 30 minutes subsequently. The reaction mixture is then cooled to -70° and 7.1 g (3.1 mL) of methyl iodide is added dropwise. The reaction is stirred at -70° for 30 minutes and then without external cooling for 10 hours. The reaction is quenched by addition of water (300 mL) and extracted with diethyl ether (3×100 mL). The combined ether extracts are extracted with 3N hydrochloric acid (3×60 mL) and the acid extracts are made basic (pH 9) with 6N sodium hydroxide. The crude product is extracted into ether (3×60 mL), and after drying (MgSO4) and solvent evaporation, 4-[1-(1-(1,2,4-triazolyl)ethyl]benzonitrile is obtained.

Workup

  1. temperatureis maintained at -20°
  2. temperatureis maintained at -50° during addition and for 30 minutes subsequently
  3. temperatureThe reaction mixture is then cooled to -70°
  4. temperaturewithout external cooling for 10 hours
  5. customThe reaction is quenched by addition of water (300 mL)
  6. extractionextracted with diethyl ether (3×100 mL)
  7. extractionThe combined ether extracts are extracted with 3N hydrochloric acid (3×60 mL)
  8. extractionThe crude product is extracted into ether (3×60 mL)
  9. customafter drying
  10. custom(MgSO4) and solvent evaporation

Sources & evidence

ORD record
ord-a3cb651ef825417cb2343b42bfe32ae5
Source dataset
uspto-grants-1995_12
Patent number
US05473078

Reaction notes

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