Benzene → Tridecane

HRID 898081Notes

Reaction equation

HRID 898081 reaction equation
[H][H].N1[CH2:14][CH2:13]NCCNCCNCC1.[CH:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH3:17][CH2:16][CH2:15][CH2:20][CH2:19][CH2:15][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:13][CH3:14]

Participants

4

Reactant 3

HCID 241BenzeneHCID 649631,4,7,10-TetraazacyclododecaneHCID 178418361HCID 178418361, compound

Product 1

HCID 12388Tridecane

Procedure

A preferred preparation of the compounds of formula IIa wherein R12 is hydrogen is to react 1,4,7,10-tetraazacyclododecane, known in the art, with dimethylformamidedimethylacetal in the presence of benzene to yield 1,4,7,10-tetraazatricyclo-[5.5,1.0]tridecane. This “tricyclic” compound is reacted with an ethanol/water mixture to yield 1-formyl-1,4,7,10-tetraazacyclododecane. This formyl compound is then reacted with t-butyl bromoacetate to yield 1-formyl-4,7,10-triscarboxymethyl-1,4,7,10-tetraazacyclododecane, tris-t-butylester. Finally, the ester groups are removed in the presence of strong acid, such as sulfuric acid, to yield a compound of formula IIa wherein R12 is hydrogen. The most preferred methods are included in Dischino, et al., Inorg. Chem., 30, 1265, 1991.

Workup

  1. customA preferred preparation of the compounds of formula IIa wherein R12

Sources & evidence

ORD record
ord-2b04ca0ceb2c43d1bfba25487a97f324
Source dataset
uspto-grants-2008_04
Patent number
US07351389B2

Reaction notes

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