Acetic Acid → N-[2-(4-Cyanophenoxy)ethyl]-N-(2-hydroxyethyl)urea

HRID 899123Notes

Reaction equation

HRID 899123 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.[O-:16][C:17]#[N:18].[K+].C(O)(=O)C>O1CCOCC1.O>[C:12]([C:11]1[CH:10]=[CH:9][C:8]([O:7][CH2:6][CH2:5][N:4]([CH2:3][CH2:2][OH:1])[C:17]([NH2:18])=[O:16])=[CH:15][CH:14]=1)#[N:13]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 11378442Potassium cyanateHCID 690686254-{2-[(2-Hydroxyethyl)amino]ethoxy}benzonitrile

Product 1

HCID 69067579N-[2-(4-Cyanophenoxy)ethyl]-N-(2-hydroxyethyl)urea

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-[2-(2-hydroxyethylamino)ethoxy]benzonitrile (5 g, 0.0242 mol; see Preparation C(ii) above) in dioxane (65 mL) and water (65 mL) was added, at rt, potassium cyanate (4.92 g, 0.0606 mol), followed by acetic acid (4.36 g, 0.0726 mol). The reaction mixture was then stirred at rt overnight, before being concentrated under reduced pressure. The resulting residue was partitioned between water and dichloromethane. The organic layer was separated, washed with water and brine, dried over sodium sulfate and then concentrated. The crude product was further purified by column chromatography. Yield: 3.5 g.

Workup

  1. concentrationbefore being concentrated under reduced pressure
  2. customThe resulting residue was partitioned between water and dichloromethane
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude product was further purified by column chromatography

Sources & evidence

ORD record
ord-a168dc81a1b7404e8bafe9bb263b6f9c
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

Loading…