HCID 86606265, compound → HCID 69031191, compound

HRID 1868442Notes

Reaction equation

HRID 1868442 reaction equation
[N+:1]([C:4]1[CH:32]=[C:31]([N+:33]([O-])=O)[CH:30]=[CH:29][C:5]=1[O:6][C:7]1[N:12]=[CH:11][N:10]=[C:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[N:8]=1)([O-])=O.[H][H]>O1CCCC1.[Pd]>[NH2:1][C:4]1[CH:32]=[C:31]([NH2:33])[CH:30]=[CH:29][C:5]=1[O:6][C:7]1[N:12]=[CH:11][N:10]=[C:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[N:8]=1

Participants

5

Reactant 2

HCID 86606265HCID 86606265, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69031191HCID 69031191, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

14.5 g of 2,4-dinitrophenoxy-6-hexadecyl-1,3,5-triazine prepared in Preparative Example 2 was dissolved in 300 ml of tetrahydrofuran, and then 1.4 g of Pd/C was added thereto. Hydrogen gas at 50 psi was fed to the mixture, and then reacted at 60° C. for 12 hours. After the reaction, the reaction mixture was filtered to remove palladium, and evaporated under reduced pressure to obtain a crude product. The crude product was recrystallized to afford pure 2,4-diaminophenoxy-6-hexadecyl-1,3,5-triazine as a white solid. The final product was relatively stable under ambient conditions. The structure of the final product was identified through 1H-NMR spectrum, and the differential scanning calorimetry (DSC) was performed (see, FIGS. 1 and 2).

Workup

  1. customreacted at 60° C. for 12 hours
  2. customAfter the reaction
  3. filtrationthe reaction mixture was filtered
  4. customto remove palladium
  5. customevaporated under reduced pressure
  6. customto obtain a crude product
  7. customThe crude product was recrystallized

Sources & evidence

ORD record
ord-bb25ca412ff044579974f32b1b54c910
Source dataset
uspto-grants-2009_12
Patent number
US07635746B2

Reaction notes

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