Water → HCID 10796999, compound

HRID 1722713Notes

Reaction equation

HRID 1722713 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:17](Br)[C:18]#[CH:19].O>C1(C)C=CC=CC=1>[CH2:19]([NH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)[C:18]#[CH:17]

Participants

6

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 8471TriethylamineHCID 133964-Aminobenzonitrile

Product 1

HCID 10796999HCID 10796999, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 4-aminobenzonitrile, 5 g (0.042 mol), triethylamine, 8.55 g (0.085 mol), and an 80% by weight solution of propargyl bromide in toluene, 12.6 g (0.085 mol), in toluene is refluxed overnight. The solution is cooled to room temperature and poured into water. The organic layer is separated, dried (sodium sulfate), filtered, and concentrated in vacuo. The residue is purified by chromatography over silica gel to give 4-(2-propynylamino)benzonitrile.

Workup

  1. customThe organic layer is separated
  2. dry with materialdried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by chromatography over silica gel

Sources & evidence

ORD record
ord-88032b7552154f32902990af335591e8
Source dataset
uspto-grants-1989_08
Patent number
US04857530

Reaction notes

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