3-Nitroaniline → HCID 22724130, compound

HRID 2230942Notes

Reaction equation

HRID 2230942 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([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]([NH:7][C:12]2[N:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:8]=[CH:9][CH:10]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 74233-NitroanilineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 744042-Chloropyrimidine

Product 1

HCID 22724130HCID 22724130, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 3-nitroaniline (6.14 g), 2-chloropyrimidine (4.85 g) and potassium carbonate (6.15 g) in dimethylsulfoxide (50 ml) was heated at 170° C. for 5 hours. 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-nitrophenylamino)pyrimidine (1.92 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-d81cbeb0a69d4ce5a4169da99356e376
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

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