Diethylenetriamine → HCID 86745183, compound

HRID 346006Notes

Reaction equation

HRID 346006 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][NH2:7].[OH-:8].[Na+].Cl[C:11]1[N:16]=[C:15]([N:17]([CH2:28][CH2:29][CH2:30][CH3:31])[CH:18]2[CH2:23][C:22]([CH3:25])([CH3:24])[NH:21][C:20]([CH3:27])([CH3:26])[CH2:19]2)[N:14]=[C:13]([N:32]2[C:37]([CH3:39])([CH3:38])[CH2:36][CH:35]([O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[CH2:34][C:33]2([CH3:48])[CH3:47])[N:12]=1>O.C1(C)C=CC=CC=1>[CH3:48][C:33]1([CH3:47])[CH2:34][CH:35]([O:8][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH3:41])[CH2:36][C:37]([CH3:38])([CH3:39])[N:32]1[C:13]1[N:14]=[C:15]([N:17]([CH2:28][CH2:29][CH2:30][CH3:31])[CH:18]2[CH2:23][C:22]([CH3:25])([CH3:24])[NH:21][C:20]([CH3:27])([CH3:26])[CH2:19]2)[N:16]=[C:11]([NH:1][CH2:2][CH2:3][N:4]([C:11]2[N:12]=[C:13]([N:32]3[C:33]([CH3:47])([CH3:48])[CH2:34][CH:35]([O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[CH2:36][C:37]3([CH3:39])[CH3:38])[N:14]=[C:15]([N:17]([CH2:28][CH2:29][CH2:30][CH3:31])[CH:18]3[CH2:19][C:20]([CH3:27])([CH3:26])[NH:21][C:22]([CH3:25])([CH3:24])[CH2:23]3)[N:16]=2)[CH2:5][CH2:6][NH:7][C:11]2[N:12]=[C:13]([N:32]3[C:33]([CH3:48])([CH3:47])[CH2:34][CH:35]([O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[CH2:36][C:37]3([CH3:38])[CH3:39])[N:14]=[C:15]([N:17]([CH2:28][CH2:29][CH2:30][CH3:31])[CH:18]3[CH2:23][C:22]([CH3:25])([CH3:24])[NH:21][C:20]([CH3:27])([CH3:26])[CH2:19]3)[N:16]=2)[N:12]=1

Participants

6

Reactant 3

HCID 8111DiethylenetriamineHCID 14798Sodium HydroxideHCID 57014857HCID 57014857, compound

Product 1

HCID 86745183HCID 86745183, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

0.71 ml of diethylenetriamine and 0.9 g of NaOH, dissolved in 3 ml of water, are added to 10.6 g of the monochloro derivative from Example 70, dissolved in 50 ml of toluene. After warming to 100°, the solvent begins to distill off. A further 50 ml of toluene and 1 g of polyethylene glycol 1000 and 0.9 g of NaOH are added and the mixture is heated with stirring for 14 h under reflux. After cooling, the reaction mixture is diluted using 100 ml of ethyl acetate and the solution is washed four times with water. The organic solution is dried over Na2SO4 and evaporated. The residue is dissolved in 50 ml of methanol, filtered through 200 g of silica gel and washed with 500 ml of methanol. The methanol solution is evaporated, the residue being a nearly colorless resin.

Workup

  1. temperatureAfter warming to 100°
  2. distillationto distill off
  3. additionA further 50 ml of toluene and 1 g of polyethylene glycol 1000 and 0.9 g of NaOH are added
  4. temperaturethe mixture is heated
  5. temperatureunder reflux
  6. temperatureAfter cooling
  7. additionthe reaction mixture is diluted
  8. washthe solution is washed four times with water
  9. dry with materialThe organic solution is dried over Na2SO4
  10. customevaporated
  11. dissolutionThe residue is dissolved in 50 ml of methanol
  12. filtrationfiltered through 200 g of silica gel
  13. washwashed with 500 ml of methanol
  14. customThe methanol solution is evaporated

Sources & evidence

ORD record
ord-b1fc6ac851624b46838b8df6ed3bd165
Source dataset
uspto-grants-1991_10
Patent number
US05059689

Reaction notes

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