Sodium Hydroxide → HCID 57088855, compound

HRID 2059132Notes

Reaction equation

HRID 2059132 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]([CH:13]2[CH2:18][C:17]([CH3:20])([CH3:19])[N:16]([CH3:21])[C:15]([CH3:23])([CH3:22])[CH2:14]2)[CH2:9][CH2:10][CH2:11][CH3:12])[N:5]=[C:4]([N:24]([CH:29]2[CH2:34][C:33]([CH3:36])([CH3:35])[N:32]([CH3:37])[C:31]([CH3:39])([CH3:38])[CH2:30]2)[CH2:25][CH2:26][CH2:27][CH3:28])[N:3]=1.[NH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][NH2:47].[OH-].[Na+]>C1(C)C(C)=CC=CC=1.O>[NH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][NH:47][C:2]1[N:7]=[C:6]([N:8]([CH:13]2[CH2:18][C:17]([CH3:20])([CH3:19])[N:16]([CH3:21])[C:15]([CH3:22])([CH3:23])[CH2:14]2)[CH2:9][CH2:10][CH2:11][CH3:12])[N:5]=[C:4]([N:24]([CH:29]2[CH2:30][C:31]([CH3:38])([CH3:39])[N:32]([CH3:37])[C:33]([CH3:35])([CH3:36])[CH2:34]2)[CH2:25][CH2:26][CH2:27][CH3:28])[N:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 16402HexamethylenediamineHCID 22256308HCID 22256308, compound

Product 1

HCID 57088855HCID 57088855, compoundYield 89.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7237O-XyleneSolvent2×

Procedure

56.4 g of 2-chloro-4,6-bis-(1,2,2,6,6-pentamethyl-4-piperidyl-butylamino)-1,3,5-triazine are introduced into a melt of 120 g of hexamethylenediamine at 80°. The reaction mixture is then stirred for 8 hours at 100° and after adding 50 ml of xylene is then stirred for 16 hours at 140°. The reaction mixture is diluted with 200 ml of xylene, a solution of 4.4 g of sodium hydroxide in 50 ml of water is added and the resulting mixture is stirred vigorously for 4 hours at room temperature. The xylene solution is separated off from the aqueous phase in a separating funnel, dried over sodium sulphate and evaporated in vacuo. 57.9 g of the 2-(6-aminohexylamino)-4,6-bis-(1,2,2,6,6-pentamethyl-4-piperidyl-butylamino)-1,3,5-triazine thus obtained are dissolved in 200 ml of xylene and the resulting solution is cooled to 5°. 5.5 g of cyanuric chloride are introduced at this temperature and the reaction mixture is stirred at 5°-10° for 1 hour. After adding 1.2 g of finely powdered sodium hydroxide, the temperature is raised to 35°-40° and the mixture is stirred for 2 hours at this temperature. After adding a further portion of 1.2 g of sodium hydroxide, the reaction mixture is slowly heated to the reflux temperature. After 3 hours under reflux, a final portion of 1.4 g of sodium hydroxide is added and the reaction mixture is then stirred under reflux for 16 hours. After cooling, 200 ml of water are added, the mixture is stirred well for 15 minutes, the aqueous solution is separated off and the xylene solution is washed with 3 times 100 ml of water. The xylene solution is evaporated in vacuo and the residue is then dried under a high vacuum (130°/0.001 mm Hg). The resulting, pale yellowish mass can be comminuted to a virtually colourless powder. The light stabiliser having the above structural formula melts at about 125°.

Workup

  1. stirringis then stirred for 16 hours at 140°
  2. stirringthe resulting mixture is stirred vigorously for 4 hours at room temperature
  3. customThe xylene solution is separated off from the aqueous phase in a separating funnel
  4. dry with materialdried over sodium sulphate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-8353dde9281d4fefa3cadb970d2c46f2
Source dataset
uspto-grants-1982_03
Patent number
US04322337

Reaction notes

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