Glyoxal → Ammonia

HRID 1782392Notes

Reaction equation

HRID 1782392 reaction equation
[N:1]12[CH2:26][CH2:25][NH:24][CH2:23][CH2:22][NH:21][CH2:20][CH2:19][N:10]([CH2:11][CH2:12][NH:13][CH2:14][CH2:15][NH:16][CH2:17][CH2:18]1)[CH2:9][CH2:8][NH:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2.NCCN(CCN)CCN.C(C=O)=O.[N:41]12[CH2:66][CH2:65][N:64]=[CH:63][CH:62]=[N:61][CH2:60][CH2:59][N:50]([CH2:51][CH2:52][N:53]=[CH:54][CH:55]=[N:56][CH2:57][CH2:58]1)[CH2:49][CH2:48][N:47]=[CH:46][CH:45]=[N:44][CH2:43][CH2:42]2>C(N(CC)CC)C.C(O)(C)C>[NH3:1].[N:41]12[CH2:42][CH2:43][NH:44][CH2:45][CH2:46][NH:47][CH2:48][CH2:49][N:50]([CH2:59][CH2:60][NH:61][CH2:62][CH2:63][NH:64][CH2:65][CH2:66]1)[CH2:51][CH2:52][NH:53][CH2:54][CH2:55][NH:56][CH2:57][CH2:58]2.[N:1]12[CH2:18][CH2:17][N:16]=[CH:15][CH:14]=[N:13][CH2:12][CH2:11][N:10]([CH2:9][CH2:8][N:7]=[CH:6][CH:5]=[N:4][CH2:3][CH2:2]1)[CH2:19][CH2:20][N:21]=[CH:22][CH:23]=[N:24][CH2:25][CH2:26]2

Participants

9

Reactant 4

HCID 7860Glyoxal2×HCID 77731Tris(2-aminoethyl)amineHCID 5255750HCID 5255750, compound3×HCID 6394059HCID 6394059, compound

Product 3

HCID 222AmmoniaHCID 5255750HCID 5255750, compoundHCID 6394059HCID 6394059, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8471TriethylamineSolvent

Procedure

The present invention also relates to a process for the preparation of 1,4,7,10,13,16,21,24-octaazabicyclo[8.8.8]hexacosane (1) which comprises: reacting in a non-reactive gas atmosphere a mixture of tris(2-aminoethyl)amine (tren), isopropyl alcohol (i-PrOH) and triethylamine (Et3N) with glyoxal with a first cooling of the mixture to between about −70° C. and −30° C., wherein the glyoxal is added slowly to the mixture, to prepare 1,4,7,10,13,16,21,24-octaazabicyclo[8.8.8]hexacosa, 4,6,13,15,21,23-hexaene (2); allowing the mixture including compound (2) to warm to room temperature; cooling the mixture including compound (2) with a second cooling; reacting compound (2) in a second mixture with an alkali metal in the presence of ammonia to form compound (1) from compound (2); allowing the second mixture to warm to room temperature with removal of the ammonia; and separating compound (1) from the reaction mixture.

Workup

  1. temperaturea first cooling of the mixture to between about −70° C. and −30° C.
  2. temperaturecooling the mixture

Sources & evidence

ORD record
ord-9876b5db7b444962811c98f10c017d2b
Source dataset
uspto-grants-2009_03
Patent number
US07498432B2

Reaction notes

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