Cyanuric chloride → HCID 20272144, compound

HRID 484938Notes

Reaction equation

HRID 484938 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5](Cl)=[N:4][C:2]=1[Cl:3].[CH2:10]([CH:12]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:13][NH:14][CH:15]1[CH2:20][C:19]([CH3:22])([CH3:21])[NH:18][C:17]([CH3:24])([CH3:23])[CH2:16]1)[CH3:11].[OH-].[Na+]>CC(C)=O.O>[Cl:3][C:2]1[N:1]=[C:8]([N:14]([CH2:13][CH:12]([CH2:10][CH3:11])[CH2:25][CH2:26][CH2:27][CH3:28])[CH:15]2[CH2:16][C:17]([CH3:24])([CH3:23])[NH:18][C:19]([CH3:21])([CH3:22])[CH2:20]2)[N:7]=[C:5]([N:14]([CH:15]2[CH2:16][C:17]([CH3:24])([CH3:23])[NH:18][C:19]([CH3:21])([CH3:22])[CH2:20]2)[CH2:13][CH:12]([CH2:10][CH3:11])[CH2:25][CH2:26][CH2:27][CH3:28])[N:4]=1

Participants

6

Reactant 3

HCID 7954Cyanuric chlorideHCID 14798Sodium HydroxideHCID 20272156N-(2-Ethylhexyl)-2,2,6,6-tetramethyl-4-piperidinamine

Product 1

HCID 20272144HCID 20272144, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent2×

Procedure

A suspension of 9.2 g of cyanuric chloride in 60 ml of acetone and 20 ml of water was added dropwise, with stirring, at 20°-25° C. to a solution of 29.5 g of 4-(2-ethylhexylamino)-2,2,6,6-tetramethylpiperidine in 50 ml of acetone, after which a solution of 4.2 g of sodium hydroxide in 20 ml of water was added to the mixture. The resulting reaction mixture was then stirred for 4 hours at 45°-50° C. At the end of this time, the acetone was distilled off and the oily residue was extracted with ethyl acetate. The extract was dried over anhydrous potassium carbonate, and the ethyl acetate was distilled off. The resulting oil was purified by column chromatography through silica gel, eluted with a 4:1 by volume mixture of hexane and ethyl acetate, to give the title compound as a colourless oil. The Rf value of this compound on thin layer chromatography was 0.62, using silica gel and using, as developing solvent, a 4:1:0.4 by volume mixture of ethyl acetate, methanol and triethylamine.

Workup

  1. additionwas added dropwise
  2. customThe resulting reaction mixture
  3. distillationAt the end of this time, the acetone was distilled off
  4. extractionthe oily residue was extracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous potassium carbonate
  6. distillationthe ethyl acetate was distilled off
  7. customThe resulting oil was purified by column chromatography through silica gel
  8. washeluted with a 4:1 by volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-2eb00fd8531c4b0196c3104b697cc214
Source dataset
uspto-grants-1985_08
Patent number
US04533688

Reaction notes

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