Aniline → HCID 791000, compound

HRID 1269368Notes

Reaction equation

HRID 1269368 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:14]=[C:13](Cl)[N:12]=[C:11]([Cl:16])[N:10]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(OCC)(=O)C>C1(C)C=CC=CC=1.C1OCCOCCOCCOCCOCCOC1>[Cl:16][C:11]1[N:10]=[C:9]([NH:8][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[N:14]=[C:13]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:12]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 167632272-29-9

Product 1

HCID 791000HCID 791000, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 1140TolueneSolvent2×

Procedure

To a mixture of (4-chloro-phenyl)-(4,6-dichloro-[1,3,5]triazin-2-yl)-amine (3.97 g, 14.4 mmol), potassium carbonate (2.20 g, 15.9 mmol) and 18-crown-6 (46 mg, 0.17 mmol) in toluene (25 ml), cooled in an ice bath, was added a solution of aniline (1.4 ml, 15.4 mmol) in toluene (10 ml) over 15 minutes. After stirring at room temperature for 24 hours, the mixture was treated with ethyl acetate (35 ml) and filtered through a pad of celite under suction. The filtrate was concentrated under vacuum and the residue was recrystallized (chloroform) to give 6-Chloro-N-(4-chlorophenyl)-N′-phenyl-[1,3,5]triazine-2,4-diamine (2.20 g, 46% yield) as a white solid. 1H NMR (d6-DMSO) δ 10.1–10.4 (2H, br s), 7.5–7.8 (4H, br s), 7.3–7.5 (4H, m), 7.15–7.05 (1H, m), ESMS m/z 330 (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. customthe residue was recrystallized (chloroform)

Sources & evidence

ORD record
ord-1bdd5405ee7e4983a448abb10d17b1ef
Source dataset
uspto-grants-2007_04
Patent number
US07199238B2

Reaction notes

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