Triethylamine → HCID 22911396, compound

HRID 1378644Notes

Reaction equation

HRID 1378644 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]([C:10]#[N:11])=[C:5]([CH3:9])OCC.[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[C:15]=1[NH:22][NH2:23].C(N(CC)CC)C>C(O)(=O)C.C(Cl)Cl.O>[CH3:1][O:2][C:3]([C:4]1[C:5]([CH3:9])=[N:23][N:22]([C:15]2[C:16]([Cl:21])=[CH:17][C:18]([Cl:20])=[CH:19][C:14]=2[Cl:13])[C:10]=1[NH2:11])=[O:12]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 79234(2,4,6-Trichlorophenyl)hydrazineHCID 53750306HCID 53750306, compound

Product 1

HCID 22911396HCID 22911396, compoundYield 45.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 21908982Water methylene chlorideSolvent

Procedure

To a solution of 2-cyano-3-methyl-3-ethoxy-acrylic acid methyl ester (3.5 g, 0.021 mol) in glacial acetic acid (20 ml), 2,4,6-trichlorophenylhydrazine (4.38 g, 0.021 mol) was added with stirring, followed by triethylamine (2.0 ml, 1.46 g, 0.014 mol). The reaction was refluxed for 13 hours. Solvent removal in vacuo afforded a dark oil, which was dissolved in methylene chloride/water (100 ml of each). The separated organic phase was extracted with an equal volume of water, dried over anhydrous sodium sulfate, and concentrated in vacuo to an orange oil (5.8 g). Flash chromatography of the entire sample (silica gel, 40 micron mesh; elution with ethyl acetate/hexane=1:3 in volume) afforded the title compound (3.20 g) as a light-orange amorphous solid. Thin layer chromatography (TLC) Rf (silica gel plates, u.v. detection, ethyl acetate/hexane=1:3 in volume): 0.43.

Workup

  1. temperatureThe reaction was refluxed for 13 hours
  2. customSolvent removal in vacuo
  3. customafforded a dark oil, which
  4. extractionThe separated organic phase was extracted with an equal volume of water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo to an orange oil (5.8 g)
  7. washFlash chromatography of the entire sample (silica gel, 40 micron mesh; elution with ethyl acetate/hexane=1:3 in volume)

Sources & evidence

ORD record
ord-280ed2e2340f49edbb7a496a7997c485
Source dataset
uspto-grants-1997_09
Patent number
US05668145

Reaction notes

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