1,2-Dimethylhydrazine dihydrochloride → 6-(N,N'-dimethyl-hydrazino)-N,N'-dipropyl-[1,3,5]triazine-2,4-diamine

HRID 530052Notes

Reaction equation

HRID 530052 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[N:5]=[C:4]([NH:12][CH2:13][CH2:14][CH3:15])[N:3]=1.Cl.Cl.[CH3:18][NH:19][NH:20][CH3:21].[OH-].[Na+]>O1CCOCC1.O>[CH2:13]([NH:12][C:4]1[N:5]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[N:7]=[C:2]([N:19]([CH3:18])[NH:20][CH3:21])[N:3]=1)[CH2:14][CH3:15]

Participants

6

Reactant 3

HCID 93801,2-Dimethylhydrazine dihydrochlorideHCID 14798Sodium HydroxideHCID 183046-chloro-2-N,4-N-dipropyl-1,3,5-triazine-2,4-diamine

Product 1

HCID 573781346-(N,N'-dimethyl-hydrazino)-N,N'-dipropyl-[1,3,5]triazine-2,4-diamineYield 42.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-chloro-N-(4,6-bis-(n-propylamino)-[1,3,5]triazine (XXXIV) (2.50 g, 10.88 mmol), N,N′-dimethyl-hydrazine dihydrochloride (2.89 g, 21.76 mmol) and NaOH (2.18 g, 54.40 mmol) in 1,4-dioxane (40 mL) and water (20 mL) was heated at 60° C. for 18 h. The volatiles were removed under reduced pressure. Saturated NaHCO3 solution (100 mL) was added to the residue, the mixture was extracted with EtOAc (3×50 mL). The combined organic extracts were washed with water (75 mL), brine (75 mL) and dried over Na2SO4. The solvent was removed under reduced pressure and the crude product was purified by flash column chromatography using gradient elution (CH2Cl2/EtOH (99:1) to CH2Cl2/EtOH (95:5)) to yield N-(4,6-Bis-propylamino-[1,3,5]triazin-2-yl)-N,N′-dimethyl-hydrazine (1.17 g, 42%). 200 MHz 1H NMR (DMSO-d6, ppm): 6.81-6.44 (2H, m), 5.31 (1H, br s), 3.24-3.08 (4H, m), 3.05 (3H, s), 2.47-2.40 (3H, m), 1.57-1.37 (4H, m), 0.84 (6H, t, J=7.4 Hz). ESI-MS (m/z): 254 [M+H]+.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. additionSaturated NaHCO3 solution (100 mL) was added to the residue
  3. extractionthe mixture was extracted with EtOAc (3×50 mL)
  4. washThe combined organic extracts were washed with water (75 mL), brine (75 mL)
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed under reduced pressure
  7. customthe crude product was purified by flash column chromatography
  8. washelution (CH2Cl2/EtOH (99:1) to CH2Cl2/EtOH (95:5))

Sources & evidence

ORD record
ord-89dce33b835541da805d6779a07dab3c
Source dataset
uspto-grants-2016_05
Patent number
US09351972B2

Reaction notes

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