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

HRID 1003144

Reaction equation

HRID 1003144 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

51.5 g (500 mmol) of diethylenetriamine and 139 ml (1 mol) of triethylamine are dissolved in dichloromethane and mixed at -20° C. with 161 g of benzyl cyanoformate (Fluka) in dichloromethane and then stirred overnight at room temperature. After the reaction is completed, concentration by evaporation is performed 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, and the precipitate is filtered off and dried.

Workup

  1. concentrationconcentration
  2. customby evaporation
  3. washthe organic phase is washed with sodium carbonate solution
  4. dry with materialdried with sodium sulfate
  5. additionThe filtrate is mixed with hexane
  6. filtrationthe precipitate is filtered off
  7. customdried

Sources & evidence

ORD record
ord-45867621a1b947e884ec397565fda740
Source dataset
uspto-grants-2000_04
Patent number
US06045776

Linked notes

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