Acetone → 4-Benzyl-1,4,7,10-tetraazacyclododecane-2,6-dione

HRID 1456887Notes

Reaction equation

HRID 1456887 reaction equation
C[CH:2]([N:6]([CH:14](C)[C:15]([O-:17])=O)[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O-:5])=O.[NH2:19][CH2:20][CH2:21][NH:22][CH2:23][CH2:24][NH2:25].CC(C)=O>C(O)C>[CH2:7]([N:6]1[CH2:2][C:3](=[O:5])[NH:25][CH2:24][CH2:23][NH:22][CH2:21][CH2:20][NH:19][C:15](=[O:17])[CH2:14]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 8111DiethylenetriamineHCID 131719217dimethyl-N-benzyl-iminodiacetate

Product 1

HCID 157028294-Benzyl-1,4,7,10-tetraazacyclododecane-2,6-dioneYield 14.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 31.2 g dimethyl-N-benzyliminodiacetate in 2.5 l of dry ethanol at reflux under nitrogen was added dropwise 12.8 g of diethylenetriamine in 160 ml of dry ethanol. Reflux was carried out for a total of 137 hours. The solution was evaporated under reduced pressure leaving a yellow paste. Trituration with acetone left 5.2 g of the desired product as a colorless solid. 13C NMR (methanol, ppm vs TMS): 173.130.5, 129.130.5, 129.6, 128.8, 64.0, 46.3, 38.7. Mass spectrum (CI): m/e 291 (M+H) and 289 (M-H).

Workup

  1. temperatureReflux
  2. customwas carried out for a total of 137 hours
  3. customThe solution was evaporated under reduced pressure
  4. customleaving a yellow paste

Sources & evidence

ORD record
ord-7f1b56e8126b4ba1a8078861e01e78cc
Source dataset
uspto-grants-1998_12
Patent number
US05846519

Reaction notes

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