Cyanuric chloride → 4,6-Dichloro-N,N-dihexyl-1,3,5-triazin-2-amine

HRID 1017502

Reaction equation

HRID 1017502 reaction equation
[CH2:1]([NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[N:14]1[C:21]([Cl:22])=[N:20][C:18](Cl)=[N:17][C:15]=1[Cl:16].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.C(OCC)(=O)C.O>[Cl:16][C:15]1[N:14]=[C:21]([Cl:22])[N:20]=[C:18]([N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[N:17]=1

Participants

7

Reactant 3

HCID 7954Cyanuric chlorideHCID 8920DihexylamineHCID 10340Sodium Carbonate

Product 1

HCID 105206134,6-Dichloro-N,N-dihexyl-1,3,5-triazin-2-amine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dihexylamine (6.3 mL, 27 mmol) was added to a mixture of cyanuric chloride (5.0 g, 27 mmol) and sodium carbonate (2.9 g, 27 mmol) in acetonitrile (50 mL). The reaction mixture was heated to reflux for 16 h and then allowed to cool to ambient temperature. The mixture was diluted with ethyl acetate and water. The phases were separated and the organic phase was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The crude material was purified by flash column chromatography through silica gel (elution with 3:1 hexanes:chloroform) to afford 2,4-dichloro-6-dihexylamino-1,3,5-triazine.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 16 h
  3. customThe phases were separated
  4. washthe organic phase was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by flash column chromatography through silica gel (elution with 3:1 hexanes:chloroform)

Sources & evidence

ORD record
ord-501e28e1e79d4fe4852c1b2dc4d03aba
Source dataset
uspto-grants-2002_11
Patent number
US06479492B1

Linked notes

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