Ammonia → 4-Chloro-6-methyl-1,3,5-triazin-2-amine

HRID 1621362Notes

Reaction equation

HRID 1621362 reaction equation
[NH3:1].CO.Cl[C:5]1[N:10]=[C:9]([Cl:11])[N:8]=[C:7]([CH3:12])[N:6]=1.C1(C)C=CC=CC=1>>[Cl:11][C:9]1[N:8]=[C:7]([CH3:12])[N:6]=[C:5]([NH2:1])[N:10]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 1140TolueneHCID 160832,4-Dichloro-6-methyl-1,3,5-triazine

Product 1

HCID 305914-Chloro-6-methyl-1,3,5-triazin-2-amineYield 73%

Procedure

A solution of ammonia, 2.0M methyl alcohol (Aldrich, St. Louis, Mo.) (36.0 mL, 72 mmol) was added dropwise at room temperature (slightly exothermic) to a stirred yellow suspension of 2,4-dichloro-6-methyl-1,3,5-triazine (from Example 7) (2.94 g, 18 mmol) in toluene (20.0 mL, 188 mmol) over 1.5 h. The resulting mixture was stirred for an additional 2.5 h, concentrated and purified (ISCO, DCM to 10% MeOH in DCM) to give the desired product 4-chloro-6-methyl-1,3,5-triazin-2-amine (1.88 g, 73%) as a yellow solid. MS (API-ES) m/z 145 (M+H)+; 1H NMR (CD3OD, 300 MHz) δ 2.32 (s, 3H).

Workup

  1. concentrationconcentrated
  2. custompurified (ISCO, DCM to 10% MeOH in DCM)

Sources & evidence

ORD record
ord-c7fab7cffc0f497fb354fe1373227861
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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