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

HRID 1811774Notes

Reaction equation

HRID 1811774 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-71bdab6e22434c00befe0e7b376d17a3
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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