4-Chloroaniline → 2272-29-9

HRID 1829617Notes

Reaction equation

HRID 1829617 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-chlorophenyl)-(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 (1 H, s), 7.62 (2 H, d, J=9 Hz), 7.47 (2 H, d, J=9 Hz). 3C 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-865602a23d554544a0e61d42befa5c91
Source dataset
uspto-grants-2006_06
Patent number
US07064125B2

Reaction notes

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