Tert-Butylamine → N-tert-Butyl-4,6-dichloro-1,3,5-triazin-2-amine

HRID 1899758Notes

Reaction equation

HRID 1899758 reaction equation
[OH-].[Na+].[C:3]([NH2:7])([CH3:6])([CH3:5])[CH3:4].[N:8]1[C:15]([Cl:16])=[N:14][C:12](Cl)=[N:11][C:9]=1[Cl:10]>C1(C)C=CC=CC=1>[Cl:10][C:9]1[N:8]=[C:15]([Cl:16])[N:14]=[C:12]([NH:7][C:3]([CH3:6])([CH3:5])[CH3:4])[N:11]=1

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 7954Cyanuric chlorideHCID 14798Sodium Hydroxide2×

Product 1

HCID 176454N-tert-Butyl-4,6-dichloro-1,3,5-triazin-2-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

10 ml 0.1N sodium hydroxide solution and 6.74 g (92.25 mmol) tert.butylamine are added to 9.23 g (50 mmol) cyanuric chloride in 200 ml toluene and stirred for 1 hour at 20° C. The pH value of the reaction is monitored continuously during this period and if necessary readjusted to pH 11-12 with 1N sodium hydroxide solution. Subsequently the solvent is removed by distillation, the residue is taken up in 150 ml water, extracted twice with 150 ml ethyl acetate each time, the organic phase is dried over magnesium sulfate and the solvent is removed. The residue is dissolved in 200 ml ethyl acetate/petroleum ether (v/v 4/1), insoluble components are removed by filtration and the filtrate is concentrated by evaporation. The crude product is purified by column chromatography (silica gel Merck 60, 5×30 cm, eluant: ethyl acetate/petroleum ether (v/v 4/1).

Workup

  1. waitThe pH value of the reaction is monitored continuously during this period
  2. customSubsequently the solvent is removed by distillation
  3. extractionextracted twice with 150 ml ethyl acetate each time
  4. dry with materialthe organic phase is dried over magnesium sulfate
  5. customthe solvent is removed
  6. dissolutionThe residue is dissolved in 200 ml ethyl acetate/petroleum ether (v/v 4/1)
  7. custominsoluble components are removed by filtration
  8. concentrationthe filtrate is concentrated by evaporation
  9. customThe crude product is purified by column chromatography (silica gel Merck 60, 5×30 cm, eluant

Sources & evidence

ORD record
ord-699d3467d2274fb3a4ebc4ef1a57ff6d
Source dataset
uspto-grants-1996_11
Patent number
US05573922

Reaction notes

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