Sodium Hydroxide → 2,2'-[Hexamethylenebis[(2,2,6,6-tetramethyl-4-piperidinyl)imino]]bis(4-allyloxy-6-t-octylamino-1,3,5-triazine)

HRID 435222Notes

Reaction equation

HRID 435222 reaction equation
[NH:1]([CH:19]1[CH2:24][C:23]([CH3:26])([CH3:25])[NH:22][C:21]([CH3:28])([CH3:27])[CH2:20]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][CH:9]1[CH2:14][C:13]([CH3:16])([CH3:15])[NH:12][C:11]([CH3:18])([CH3:17])[CH2:10]1.[CH2:29]([O:32][C:33]1[N:38]=[C:37](Cl)[N:36]=[C:35]([NH:40][C:41]([CH2:44][C:45]([CH3:48])([CH3:47])[CH3:46])([CH3:43])[CH3:42])[N:34]=1)[CH:30]=[CH2:31].[OH-:49].[Na+]>C1(C)C(C)=CC=CC=1>[CH3:25][C:23]1([CH3:26])[CH2:24][CH:19]([N:1]([C:37]2[N:38]=[C:33]([O:49][CH2:31][CH:30]=[CH2:29])[N:34]=[C:35]([NH:40][C:41]([CH2:44][C:45]([CH3:46])([CH3:48])[CH3:47])([CH3:43])[CH3:42])[N:36]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]([C:37]2[N:38]=[C:33]([O:32][CH2:29][CH:30]=[CH2:31])[N:34]=[C:35]([NH:40][C:41]([CH2:44][C:45]([CH3:48])([CH3:47])[CH3:46])([CH3:43])[CH3:42])[N:36]=2)[CH:9]2[CH2:14][C:13]([CH3:16])([CH3:15])[NH:12][C:11]([CH3:17])([CH3:18])[CH2:10]2)[CH2:20][C:21]([CH3:28])([CH3:27])[NH:22]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 934191,6-Bis(2,2,6,6-tetramethyl-4-piperidylamino)hexaneHCID 20452243HCID 20452243, compound

Product 1

HCID 204522272,2'-[Hexamethylenebis[(2,2,6,6-tetramethyl-4-piperidinyl)imino]]bis(4-allyloxy-6-t-octylamino-1,3,5-triazine)Yield 68.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A stirred mixture of 4,4'(hexamethylenediimino)bis(2,2,6,6-tetramethylpiperidine) (10.0 grams; 0.025 mole), 2-allyloxy-4-chloro-6-t-octylamino-1,3,5-triazine (15.1 grams; 0.05 mole), and powdered sodium hydroxide (2.0 grams; 0.05 mole) in xylene (150 mls) is heated at reflux for 24 hours while removing by-product water by means of a trap. The reaction mixture is filtered while hot to remove insolubles. Upon cooling the filtrate, a white crystalline solid precipitates. The solid is recovered by filtration and dried to obtain 15.7 grams of the desired product, mp 210°-212° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 24 hours
  3. customwhile removing by-product water by means of a trap
  4. filtrationThe reaction mixture is filtered while hot
  5. customto remove insolubles
  6. temperatureUpon cooling the filtrate
  7. customa white crystalline solid precipitates
  8. filtrationThe solid is recovered by filtration
  9. customdried

Sources & evidence

ORD record
ord-00f27744898545709f42e3e11a37d0a1
Source dataset
uspto-grants-1983_08
Patent number
US04400505

Reaction notes

Loading…