Cyanuric chloride → N,N',N''-Tris-(3'-azidopropyl)-[1,3,5]triazine-2,4,6-triamine

HRID 421523Notes

Reaction equation

HRID 421523 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1Cl.[N:10]([CH2:13][CH2:14][CH2:15][NH2:16])=[N+:11]=[N-:12]>>[N:10]([CH2:13][CH2:14][CH2:15][NH:16][C:2]1[N:4]=[C:5]([NH:16][CH2:15][CH2:14][CH2:13][N:10]=[N+:11]=[N-:12])[N:7]=[C:8]([NH:16][CH2:15][CH2:14][CH2:13][N:10]=[N+:11]=[N-:12])[N:1]=1)=[N+:11]=[N-:12]

Participants

3

Reactant 2

HCID 7954Cyanuric chlorideHCID 1501103-Azidopropan-1-amine

Product 1

HCID 86006182N,N',N''-Tris-(3'-azidopropyl)-[1,3,5]triazine-2,4,6-triamine

Procedure

FIG. 6 is a series of schemes showing the synthesis of the monomers used in the adhesives test. The first reaction to make 1 is an N-sulfonylation of the nitrogen mustard, N,N-di(2-chloroethyl) amine, followed by an SN2 displacement of the chlorides to obtain the diazide, 1. The second reaction is an N-propargylation of 4-methyl-benzenesulfonamide under mild conditions to give the diacetylene, 2. The last reaction is the displacement of the chlorides of cyanuric chloride with 3-azidopropylamine to give the triamino-1,3,5-triazine 5.

Workup

  1. customThe last reaction

Sources & evidence

ORD record
ord-1a7b928f1d7b439a86576cc57df4ac77
Source dataset
uspto-grants-2012_01
Patent number
US08101238B2

Reaction notes

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