Benzene → Tridecane

HRID 1856600Notes

Reaction equation

HRID 1856600 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 I wherein Y is NH and R2 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-triscarboxy-methyl-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 I wherein Y is NH and R2 is hydrogen.

Workup

  1. customA preferred preparation of the compounds of formula I wherein Y

Sources & evidence

ORD record
ord-a7975bdd05a941f8a46788946a544fae
Source dataset
uspto-grants-2000_11
Patent number
US06143274

Reaction notes

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