Triethylamine → HCID 12150557, compound

HRID 2406112Notes

Reaction equation

HRID 2406112 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][NH2:10].C(O[CH:14]=[C:15]([C:18]#[N:19])[C:16]#[N:17])C.C(N(CC)CC)C>CO>[NH2:19][C:18]1[N:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[CH3:2])[N:10]=[CH:14][C:15]=1[C:16]#[N:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 671522-(Ethoxymethylene)propanedinitrileHCID 71554o-Tolylhydrazinium(1+) chloride

Product 1

HCID 12150557HCID 12150557, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10.2 g (64.4 mmol) of 2-methylphenylhydrazine hydrochloride are suspended with 7.8 g (64.4 mmol) of ethoxymethylenemalononitrile in 100 ml of methanol, and 26.9 ml (193.3 mmol) of triethylamine are added. The reaction mixture is heated to reflux overnight, during which a clear solution forms. The solution is subsequently distilled off under reduced pressure, and the crude product is purified by column chromatography (silica gel, mobile phase dichloromethane). 10.8 g (85% of theory) of the desired product are obtained.

Workup

  1. additionare added
  2. temperatureThe reaction mixture is heated
  3. temperatureto reflux overnight, during which a clear solution forms
  4. distillationThe solution is subsequently distilled off under reduced pressure
  5. customthe crude product is purified by column chromatography (silica gel, mobile phase dichloromethane)

Sources & evidence

ORD record
ord-e92987e2a5984d0a9be6acbba74587cc
Source dataset
uspto-grants-2014_08
Patent number
US08809348B2

Reaction notes

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