Cyanuric chloride → 4,6-dichloro-N-methyl-1,3,5-triazin-2-amine

HRID 2375304Notes

Reaction equation

HRID 2375304 reaction equation
[N:1]1[C:8]([Cl:9])=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].Cl.[CH3:11][NH2:12]>C1COCC1.CCN(C(C)C)C(C)C>[Cl:9][C:8]1[N:1]=[C:2]([Cl:3])[N:4]=[C:5]([NH:12][CH3:11])[N:7]=1

Participants

5

Reactant 2

HCID 7954Cyanuric chlorideHCID 6364545Methylamine hydrochloride

Product 1

HCID 3122014,6-dichloro-N-methyl-1,3,5-triazin-2-amineYield 97.7%

Reagents, catalysts & solvents 2

HCID 81531DiisopropylethylamineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

Cyanuric chloride (10 g, 54.3 mmol, 1 equiv.) was dissolved in THF (200 mL) and cooled to −70° C. DIPEA (36.3 mL, 1.42 mmol, 2 equiv.) and methylamine hydrochloride (3.7 g, 1 equiv.) were added to the reaction mixture, which was stirred 2 h at −70° C. and 1 h at rt. The THF was removed under reduced pressure and the remaining material was taken up in DCM and washed with water. The organic layer was dried with MgSO4 and the DCM removed to give a colourless powder (9.5 g, 97%).

Workup

  1. customThe THF was removed under reduced pressure
  2. washwashed with water
  3. dry with materialThe organic layer was dried with MgSO4
  4. customthe DCM removed

Sources & evidence

ORD record
ord-7a4e9714e00148069f4398f5d5d931b4
Source dataset
uspto-grants-2008_12
Patent number
US07465736B2

Reaction notes

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