Diisopropylethylamine → N-[2-(3-cyanophenoxy)ethyl]bromoacetamide

HRID 747744Notes

Reaction equation

HRID 747744 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[C:8]#[N:9].C(N(C(C)C)CC)(C)C.[Br:22][CH2:23][C:24](Cl)=[O:25]>O1CCCC1>[C:8]([C:7]1[CH:6]=[C:5]([CH:12]=[CH:11][CH:10]=1)[O:4][CH2:3][CH2:2][NH:1][C:24](=[O:25])[CH2:23][Br:22])#[N:9]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 89602Bromoacetyl chlorideHCID 109098773-(2-Aminoethoxy)benzonitrile

Product 1

HCID 68829328N-[2-(3-cyanophenoxy)ethyl]bromoacetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.50 g (9.26 mmol) of 3-(2-aminoethoxy)benzonitrile and 1.77 ml (10.2 mmol) of diisopropylethylamine were dissolved in 15 ml of tetrahydrofuran. A solution of 0.92 ml (11.1 mmol) of bromoacetyl chloride in 5 ml of tetrahydrofuran was added to the obtained solution at 0° C., and they were stirred for 8 hours. The solvent was evaporated, and the residue was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-bc575cc448ba47f7a3ed511fd6c8133f
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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