1,4,7,10-Tetraazacyclododecane → HCID 18471400, compound

HRID 1580113Notes

Reaction equation

HRID 1580113 reaction equation
[NH:1]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8][NH:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[ClH:13].Cl.Cl.Cl.N1CCCCCCC[CH2:21]NNN1.C([O-])([O-])([O-])OCC>C(O)C>[Cl-:13].[CH2:2]1[CH2:3][N:4]2[C:21]3=[N+:7]([CH2:8][CH2:9][NH:10][CH2:11][CH2:12][N:1]13)[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 649631,4,7,10-TetraazacyclododecaneHCID 21565166HCID 21565166, compoundHCID 86584012Ethyl orthocarbonate

Product 1

HCID 18471400HCID 18471400, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 0.52 g of 1,4,7,10-tetraazacyclododecane, 0.32 g of tetraazacyclododecane tetrahydrochloride, 0.77 g of ethyl orthocarbonate, and 5 ml of absolute ethyl alcohol was heated with stirring on a steam bath (ca. 100°C) for 8 hours. The nmr spectrum of a small sample of the mixture indicated that the desired reaction was about 75-80% complete. The mixture was heated with stirring on a steam bath for 19 hours more. Volatile materials were evaporated under reduced pressure, and the residue was recrystallized from acetonitrile to give 0.20 g of 1,2,3,4,6,7,8,9-octahydro-5H-4a-azonia-2a,7,9a-triazacycloocta[cd]pentalene chloride (II) as needle-like crystals.

Workup

  1. temperaturewas heated
  2. customreaction
  3. temperatureThe mixture was heated
  4. stirringwith stirring on a steam bath for 19 hours more
  5. customVolatile materials were evaporated under reduced pressure
  6. customthe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-b661c1afec5843648105c8be36678f2d
Source dataset
uspto-grants-1976_01
Patent number
US03932451

Reaction notes

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