Water → HCID 178512056, compound

HRID 1715091Notes

Reaction equation

HRID 1715091 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([Mg]Br)C.[Cl:21][C:22]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:23]=1[C:24]#[N:25].O>C1COCC1>[CH2:2]([O:9][C:10]1[CH:11]=[CH:12][C:13]([NH:14][C:24](=[NH:25])[C:23]2[CH:26]=[CH:27][C:28]([Cl:30])=[CH:29][C:22]=2[Cl:21])=[CH:15][CH:16]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 810502,4-DichlorobenzonitrileHCID 27238314-Benzyloxyaniline hydrochlorideHCID 178418443HCID 178418443, compound

Product 1

HCID 178512056HCID 178512056, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Benzyloxyaniline hydrochloride (5.0 g, 21.2 mmol) was dropwise added to a solution of ethylmagnesium bromide (44.5 ml, 1M in THF, 44.5 mmol) in 25 ml dry TIHF under nitrogen atmosphere. After stirring for 20 minutes a solution of 2,4-dichlorobenzonitrile (3.65 g, 21.2 mmol) in 25 ml THF was added. The reaction mixture was stirred for 20 hours at room temperature. Water (50 ml) was carefully added. Extraction with EtOAc (2×100 ml), drying (Na2SO4), filtration and evaporation to dryness afforded 7.7 g (98%) of the title compound.

Workup

  1. customdry TIHF under nitrogen atmosphere
  2. additionwas added
  3. extractionExtraction with EtOAc (2×100 ml)
  4. customdrying
  5. filtration(Na2SO4), filtration and evaporation to dryness

Sources & evidence

ORD record
ord-32747329bdb14331baed5446f240c5f1
Source dataset
uspto-grants-2010_09
Patent number
US07799804B2

Reaction notes

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