Ethyl Acetate → HCID 22724181, compound

HRID 2086765Notes

Reaction equation

HRID 2086765 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Cl[C:12]1[N:17]=[CH:16][CH:15]=[CH:14][N:13]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CS(C)=O.O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][C:12]1[N:17]=[CH:16][CH:15]=[CH:14][N:13]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 111373-NitrophenolHCID 11430Potassium CarbonateHCID 744042-Chloropyrimidine

Product 1

HCID 22724181HCID 22724181, compoundYield 76.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 3-nitrophenol (6.85 g), 2-chloropyrimidine (5.13 g) and potassium carbonate (6.81 g) in dimethylsulfoxide (50 ml) was heated at 150° C. for 30 minutes. The mixture was cooled and poured into a mixture of ethyl acetate and water. The organic phase was washed with brine, dried over magnesium sulfate and concentrated. The resulting solid was collected and washed with isopropyl ether to give 2-(3-nitrophenoxy)pyrimidine (7.41 g).

Workup

  1. temperatureThe mixture was cooled
  2. washThe organic phase was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe resulting solid was collected
  6. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-3cee62611aad4a229db092a388960225
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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