Cyanuric chloride → HCID 20272124, compound

HRID 484937Notes

Reaction equation

HRID 484937 reaction equation
[CH2:1]([NH:13][CH:14]1[CH2:19][C:18]([CH3:21])([CH3:20])[NH:17][C:16]([CH3:23])([CH3:22])[CH2:15]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[N:24]1[C:31](Cl)=[N:30][C:28](Cl)=[N:27][C:25]=1[Cl:26].C(=O)([O-])[O-].[K+].[K+]>C1(C)C(C)=CC=CC=1>[Cl:26][C:25]1[N:24]=[C:31]([N:13]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH:14]2[CH2:15][C:16]([CH3:22])([CH3:23])[NH:17][C:18]([CH3:21])([CH3:20])[CH2:19]2)[N:30]=[C:28]([N:13]([CH:14]2[CH2:15][C:16]([CH3:23])([CH3:22])[NH:17][C:18]([CH3:20])([CH3:21])[CH2:19]2)[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[N:27]=1

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 11430Potassium CarbonateHCID 22902700HCID 22902700, compound

Product 1

HCID 20272124HCID 20272124, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

A solution of 35.7 g of 4-dodecylamino-2,2,6,6-tetramethylpiperidine in 50 ml of xylene was added dropwise at 20°-25° C. to a solution of 9.2 g of cyanuric chloride in 250 ml of xylene. The mixture was stirred for 1.5 hours at the same temperature and then for 5 hours at 50°-55° C. At the end of this time, the reaction mixture was neutralised with an aqueous solution of potassium carbonate, and the xylene layer was separated and dried over anhydrous potassium carbonate. The xylene was distilled off and the resulting oil was purified by column chromatography through silica gel eluted with a 20:20:3:1 by volume mixture of ethyl acetate, benzene, ethanol and triethylamine to give the title compound as an oil. The Rf value of this compound on thin layer chromatography was 0.28, using silica gel and using, as developing solvent, a 20:20:3:1 by volume mixture of ethyl acetate, benzene, ethanol and triethylamine.

Workup

  1. waitfor 5 hours at 50°-55° C
  2. customthe xylene layer was separated
  3. dry with materialdried over anhydrous potassium carbonate
  4. distillationThe xylene was distilled off
  5. customthe resulting oil was purified by column chromatography through silica gel
  6. washeluted with a 20:20:3:1 by volume mixture of ethyl acetate, benzene, ethanol and triethylamine

Sources & evidence

ORD record
ord-6de1130252ed4c349ed9b073e538b849
Source dataset
uspto-grants-1985_08
Patent number
US04533688

Reaction notes

Loading…