Triethylenetetramine → 1,8-Bis[beta-(3,5-di-t-butyl-4-hydroxy phenyl) propionamido]-3,6-diazaoctane

HRID 1833332Notes

Reaction equation

HRID 1833332 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][CH2:17][C:18](Cl)=[O:19])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[NH2:21][CH2:22][CH2:23][NH:24][CH2:25][CH2:26][NH:27][CH2:28][CH2:29][NH2:30]>C(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][CH2:17][C:18]([NH:21][CH2:22][CH2:23][NH:24][CH2:25][CH2:26][NH:27][CH2:28][CH2:29][NH:30][C:18](=[O:19])[CH2:17][CH2:16][C:7]2[CH:8]=[C:9]([C:12]([CH3:13])([CH3:15])[CH3:14])[C:10]([OH:11])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=2)=[O:19])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 5565TriethylenetetramineHCID 156069683-(3,5-Di-tert-butyl-4-hydroxyphenyl)propionyl chloride

Product 1

HCID 538563861,8-Bis[beta-(3,5-di-t-butyl-4-hydroxy phenyl) propionamido]-3,6-diazaoctane

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 10340Sodium CarbonateSolvent

Procedure

0.02 moles β-(3,5-di-t-butyl-4-hydroxy phenyl) propionyl chloride in 25 ml methylene chloride was added to a stirred mixture containing a solution of 0.02 mol triethylene tetramine in 125 ml methylene chloride and 25 ml 10% sodium carbonate. The mixture was stirred for two hours and then separated. The methylene chloride layer was washed with 5% sodium carbonate solution and then with water, subsequently dried over anhydrous magnesium sulfate and finally evaporated to dryness. A resinous material of 1,8-bis[β-(3,5-di-t-butyl-4-hydroxy phenyl) propionamido]-3,6-diazaoctane resulted which was pulverized to give a light brown solid having a melting point of 80°-110° C.

Workup

  1. customseparated
  2. washThe methylene chloride layer was washed with 5% sodium carbonate solution
  3. dry with materialwith water, subsequently dried over anhydrous magnesium sulfate
  4. customfinally evaporated to dryness

Sources & evidence

ORD record
ord-76ed522f6f8142a6b9c49b5c36c639e4
Source dataset
uspto-grants-1978_01
Patent number
US04066610

Reaction notes

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