Ammonia → HCID 22218975, compound

HRID 1793764Notes

Reaction equation

HRID 1793764 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]=[N:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=2)=[CH:7][C:6]=1Br.[Cu](C#N)[C:23]#[N:24].N>CN(C=O)C>[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]=[N:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=2)=[CH:7][C:6]=1[C:23]#[N:24]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 22218976HCID 22218976, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 22218975HCID 22218975, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

15 g (4-(2-hydroxyethyloxy)-3-bromo-4′-cyanoazobenzene are dissolved in 25 ml hot DMF. 4.3 g copper cyanide are then added and the reaction mixture is stirred at 140° C. for 5–6 hours. This solution is added to approx. 500 ml of a 13% aqueous ammonia solution and the precipitate is filtered off. The precipitate is dissolved in hot dioxane. The solution is filtered off from the undissolved residue, the dioxane is evaporated off on a rotary evaporator and the product is purified by chromatography on silica gel in toluene/THF (½) and recrystallized once from ethanol. The yield of 4-(2-hydroxyethyloxy)-3,4′-dicyanoazobenzene is 4.5 g. M.p.=138° C.; max=356 nm (DMF).

Workup

  1. filtrationthe precipitate is filtered off
  2. dissolutionThe precipitate is dissolved in hot dioxane
  3. filtrationThe solution is filtered off from the undissolved residue
  4. customthe dioxane is evaporated off on a rotary evaporator
  5. customthe product is purified by chromatography on silica gel in toluene/THF (½)
  6. customrecrystallized once from ethanol

Sources & evidence

ORD record
ord-cf545d6e40c44a138df70176955c79d2
Source dataset
uspto-grants-2006_04
Patent number
US07022460B2

Reaction notes

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