Benzene → Tridecane
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
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
- customA preferred preparation of the compounds of formula IIa wherein R12
Sources & evidence
- ORD record
- ord-e26908428b7e4357a6de2592e4714054
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06875864B2
Reaction notes
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