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

HRID 439640

Reaction equation

HRID 439640 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][NH2:7].C(N([CH2:13][CH3:14])CC)C.[CH:15]([O:17][CH:18](C#N)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]>ClC(Cl)C.ClCCl>[CH2:18]([O:17][C:15]([NH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][NH:7][C:15]([O:17][CH2:18][C:14]1[CH:13]=[CH:21][CH:20]=[CH:19][CH:24]=1)=[O:16])=[O:16])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 8111DiethylenetriamineHCID 8471TriethylamineHCID 22902948Cyanobenzyl formate

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

4.87 g (47.2 mmol) of 1,4,7-triazaheptane as well as 5 ml of triethylamine are dissolved in 100 ml of dichloroethane. The solution of 15.22 g (94.4 mmol) of cyanobenzyl formate in 200 ml of dichloromethane is instilled in this solution within 3 hours. It is allowed to stir for 2 more days at room temperature, then evaporated to dryness in a vacuum, taken up in diethyl ether and washed with sodium bicarbonate solution. The ether solution is dried on sodium sulfate and evaporated to dryness in a vacuum. The residue is crystallized from a little ethanol. The title compound crystallizes into white needles. Yield: 11.46 g (65.7% of theory) Melting point: 73°-75° C. Elementary analysis: Cld: C 64.67 H 6.78 N 11.31 Fnd: C 64.82 H 6.64 N 11.28

Workup

  1. customevaporated to dryness in a vacuum
  2. washwashed with sodium bicarbonate solution
  3. dry with materialThe ether solution is dried on sodium sulfate
  4. customevaporated to dryness in a vacuum
  5. customThe residue is crystallized from a little ethanol
  6. customThe title compound crystallizes into white needles

Sources & evidence

ORD record
ord-6ac3c6418cea49e387abfe8f7bb26db8
Source dataset
uspto-grants-1996_05
Patent number
US05514810

Linked notes

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