Toluene → HCID 3353880, compound

HRID 1793931Notes

Reaction equation

HRID 1793931 reaction equation
[Cl:1][C:2]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:3]=1[CH:4]=[C:5]([C:8]#[N:9])[C:6]#[N:7].[C:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=O)[CH3:16].C([O-])(=O)C.[NH4+:28].C1(C)C=CC=CC=1>C(OCC)(=O)C>[NH2:9][C:8]1[N:28]=[C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[C:4]([C:3]2[CH:10]=[CH:11][C:12]([Cl:14])=[CH:13][C:2]=2[Cl:1])[C:5]=1[C:6]#[N:7]

Participants

6

Reactant 4

HCID 1140TolueneHCID 7410AcetophenoneHCID 180892,4-DichlorobenzylidenemalononitrileHCID 517165Ammonium Acetate

Product 1

HCID 3353880HCID 3353880, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(2,4-dichloro-benzylidene)-malononitrile (1.125 g, 5 mmol), acetophenone (601 mg, 5 mmol), ammonium acetate (578 mg, 7.5 mmol), and toluene (5 ml) was stirred for 3 h at reflux. Upon cooling to room temperature, the mixture was taken up in ethyl acetate and extracted with satd. NaHCO3, water, and satd. NaCl, and dried over Na2SO4. The solvent was then evaporated and the title compound (600 mg, 35%), MS: m/e=339.5 (M+H+), was isolated from the residue by column chromatography (silica gel, hexanes, ethyl acetate).

Workup

  1. temperatureat reflux
  2. extractionextracted with satd
  3. dry with materialNaCl, and dried over Na2SO4
  4. customThe solvent was then evaporated

Sources & evidence

ORD record
ord-8ab3bc8e1b6a4f72b9625b783858b47d
Source dataset
uspto-grants-2006_04
Patent number
US07022718B2

Reaction notes

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