4-Chloroaniline → 2272-29-9

HRID 1269367Notes

Reaction equation

HRID 1269367 reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5]([Cl:6])=[N:4][C:2]=1Cl.C(=O)([O-])[O-].[K+].[K+].[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1.C(OCC)(=O)C>C1(C)C=CC=CC=1.C1OCCOCCOCCOCCOCCOC1>[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH:21][C:2]2[N:1]=[C:8]([Cl:9])[N:7]=[C:5]([Cl:6])[N:4]=2)=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 78124-ChloroanilineHCID 7954Cyanuric chlorideHCID 8857Ethyl AcetateHCID 11430Potassium Carbonate

Product 1

HCID 167632272-29-9Yield 53%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 1140TolueneSolvent2×

Procedure

To a mixture of cyanuric chloride (5.15 g, 27.9 mmol), potassium carbonate (3.98 g, 28.8 mmol) and 18-crown-6 (158 mg, 0.60 mmol) in toluene (40 ml), cooled in an ice bath, was added a solution of 4-chloroaniline (3.61 g, 28.3 mmol) in toluene (20 ml) over 15 minutes. After stirring at room temperature for 20 hours, the mixture was treated with ethyl acetate (60 ml) and filtered through a pad of celite under suction. The filtrate was concentrated under vacuum and recrystallized (chloroform) to give (4-chloro-phenyl)-(4,6-dichloro-[1,3,5]triazin-2-yl)-amine (4.06 g, 53% yield) as a white solid. 1H NMR (d6-DMSO) δ 11.23 (1H, s), 7.62 (2H, d, J=9 Hz), 7.47 (2H, d, J=9 Hz). 13C NMR (d6-DMSO) δ 169.5, 168.5, 163.6, 135.7, 128.6, 122.5, ESMS m/z 273 (M-H)−.

Workup

  1. temperaturecooled in an ice bath
  2. filtrationfiltered through a pad of celite under suction
  3. concentrationThe filtrate was concentrated under vacuum
  4. customrecrystallized (chloroform)

Sources & evidence

ORD record
ord-7feb54b988544f63b2853f740e63c827
Source dataset
uspto-grants-2007_04
Patent number
US07199238B2

Reaction notes

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