N-Methylaniline → 4,6-dichloro-N-methyl-N-phenyl-1,3,5-triazin-2-amine

HRID 341474Notes

Reaction equation

HRID 341474 reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].[CH3:10][NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:9][C:8]1[N:1]=[C:2]([Cl:3])[N:4]=[C:5]([N:11]([CH3:10])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:7]=1

Participants

5

Reactant 3

HCID 7515N-MethylanilineHCID 7954Cyanuric chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 198964,6-dichloro-N-methyl-N-phenyl-1,3,5-triazin-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred solution of cyanuric chloride (2 g, 10.84 mmol) in DCM (40 ml) at 0-5° C. was added dropwise a solution of N-methyl aniline (1.16 ml, 10.84 mmol) and DIPEA (2.08 ml, 12.26 mmol) in DCM (30 ml). The resulting mixture was allowed to warm to room temperature and stirred for 48 h. The reaction mixture was diluted with DCM (40 ml) the solution was then extracted with 2M aq. HCl (2×40 mL) and saturated brine (30 mL) and dried further over anhydrous sodium sulfate. The organic phase was evaporated to dryness to furnish the title compound as an off white solid (2.726 g, 99%). Method C HPLC-MS: MH+ requires m/z=255. Found: m/z=255, Rt=1.48 min (100%). 1H NMR (500 MHz, CDCl3) δ ppm 7.35-7.42 (2H, m), 7.29 (1H, d), 7.15-7.21 (3H, m), 3.48 (3H, s).

Workup

  1. extractionwas then extracted with 2M aq. HCl (2×40 mL) and saturated brine (30 mL)
  2. dry with materialdried further over anhydrous sodium sulfate
  3. customThe organic phase was evaporated to dryness

Sources & evidence

ORD record
ord-a56eb51abbc74bf99440b8f7cac4d4e9
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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