Diethylenetriamine → N,N''-Di-Z-diethylenetriamine

HRID 1108657Notes

Reaction equation

HRID 1108657 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][NH2:7].C(N([CH2:13][CH3:14])CC)C.C([C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])#N>ClCCl>[CH2:20]([O:19][C:17]([NH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][NH:7][C:17]([O:19][CH2:20][C:14]1[CH:13]=[CH:23][CH:22]=[CH:21][CH:26]=1)=[O:18])=[O:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 8111DiethylenetriamineHCID 8471TriethylamineHCID 79660Benzyl cyanoformate

Product 1

HCID 4367374N,N''-Di-Z-diethylenetriamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5.15 g (50 mmol) of diethylenetriamine and 13.9 ml (100 mmol) of triethylamine are dissolved in dichloromethane and mixed at -20° C. with 16.1 g of benzyl cyanoformate (Fluka) in dichloromethane, and then it is stirred overnight at room temperature. After the reaction has been completed, it is evaporated during draw-off, the residue is taken up in diethyl ether, the organic phase is washed with sodium carbonate solution and dried with sodium sulfate. The filtrate is mixed with hexane, the precipitate is filtered off and dried.

Workup

  1. customit is evaporated during draw-off, the residue
  2. washthe organic phase is washed with sodium carbonate solution
  3. dry with materialdried with sodium sulfate
  4. additionThe filtrate is mixed with hexane
  5. filtrationthe precipitate is filtered off
  6. customdried

Sources & evidence

ORD record
ord-87bb300a9aba4cda989453046d17f2fe
Source dataset
uspto-grants-2000_05
Patent number
US06068831

Reaction notes

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