HCID 19069522, compound → HCID 19069528, compound

HRID 1957293Notes

Reaction equation

HRID 1957293 reaction equation
[CH3:1][O:2][CH:3](OC)[CH2:4][CH2:5][CH2:6][NH:7][C:8]1[N:13]=[C:12]([NH:14][CH2:15][CH2:16][CH2:17][CH:18]([O:21][CH3:22])OC)[N:11]=[C:10]([NH:23][CH2:24][CH2:25][CH2:26][CH:27](OC)[O:28][CH3:29])[N:9]=1>C(Cl)Cl>[CH3:29][O:28][CH:27]1[CH2:26][CH2:25][CH2:24][N:23]1[C:10]1[N:11]=[C:12]([N:14]2[CH2:15][CH2:16][CH2:17][CH:18]2[O:21][CH3:22])[N:13]=[C:8]([N:7]2[CH2:6][CH2:5][CH2:4][CH:3]2[O:2][CH3:1])[N:9]=1

Participants

3

Reactant 1

HCID 19069522HCID 19069522, compound

Product 1

HCID 19069528HCID 19069528, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of strongly acidic AMBERLYST® 15 ion-exchange resin (6.6 g), a product of Rohm and Haas Company, Philadelphia, Pa., and methylene chloride (20 ml) in a 100 ml flask equipped with a magnetic stirrer, condenser and nitrogen inlet was stirred for 5 minutes and thereafter, the solvent was removed by decanting. A solution of the 2,4,6-tris-(4,4-dimethoxybutylamino)-1,3,5-triazine of Example 1 (6.1 g, 0.0129 mole) in methylene chloride (120 ml) was then added in one portion to the flask and the resulting mixture was stirred at room temperature under a nitrogen atmosphere for 1.5 hours. The ion exchange resin was then filtered and the volatiles removed under reduced pressure to give 2,4,6-tris-(2-methoxypyrrolidinyl)-1,3,5-triazine (2.7 g, 56 % isolated yield) as a glassy solid. The structure of the product was confirmed by nuclear magnetic resonance (NMR) and mass spectroscopic (MS) analysis: 1H NMR (5 ): 5.6 (m, 1 H, --NCHOCH3); 3.8 -3.2 (m, 5H, --OCH3 and --NCH2); 2.2-1.6 (m, 4H,--CH2 --); 13C NMR (ppm): 165, 88, 56, 46, 32, 22; MS (m/e, MH): 379.

Workup

  1. customthe solvent was removed
  2. customby decanting
  3. stirringthe resulting mixture was stirred at room temperature under a nitrogen atmosphere for 1.5 hours
  4. filtrationThe ion exchange resin was then filtered
  5. customthe volatiles removed under reduced pressure

Sources & evidence

ORD record
ord-72024e4739f6484f9484b720e6eecf3c
Source dataset
uspto-grants-1998_07
Patent number
US05783642

Reaction notes

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