2,4,6-Trimethylpyridine → HCID 14533895, compound

HRID 1901812Notes

Reaction equation

HRID 1901812 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5]([Cl:6])=[N:4][C:2]=1[Cl:3].S([O-])([O-])(=O)=O.[Na+].[Na+].[C:17]([C:21]1[CH:22]=[C:23]([SH:32])[CH:24]=[C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:26]=1[OH:27])([CH3:20])([CH3:19])[CH3:18].CC1C=C(C)N=C(C)C=1>CC(C)=O.ClC1C=CC=CC=1>[Cl:3][C:2]1[N:4]=[C:5]([Cl:6])[N:7]=[C:8]([S:32][C:23]2[CH:22]=[C:21]([C:17]([CH3:18])([CH3:19])[CH3:20])[C:26]([OH:27])=[C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:24]=2)[N:1]=1

Participants

7

Reactant 4

HCID 79532,4,6-TrimethylpyridineHCID 7954Cyanuric chlorideHCID 24436Sodium SulfateHCID 703702,6-Di-tert-butyl-4-mercaptophenol

Product 1

HCID 14533895HCID 14533895, compoundYield 43.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 7964ChlorobenzeneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 0.1 mol of cyanuric chloride in 120 ml of acetone are added 3 g of anhydrous sodium sulfate and the mixture is cooled to 0° C. A solution of 0.1 mol of 3,5-di-tert-butyl-4hydroxythiophenol in 25 ml of chlorobenzene is then run in. Afterwards 12.7 g of s-collidine are added dropwise at 5° C. over 20 minutes to the reaction mixture. The reaction is brought to completion by stirring for 30 minutes at 5° C. and for 2 hours at room temperature. The reaction mixture is then filtered and, after washing with 100 ml of acetone, the filtrate is stirred into a mixture of 400 g of ice and 900 ml of water, acidified with dilute hydrochloric acid (weakly acid reaction to litmus paper), and extracted repeatedly with ethyl acetate. Conventional working up and recystallisation from hexane/acetone gives 16.9 g of 2,4-dichloro-6-(3',5'-di-tert-butyl-4'-hydroxyphenylsulfanyl)-s-triazine.

Workup

  1. filtrationThe reaction mixture is then filtered
  2. washafter washing with 100 ml of acetone
  3. stirringthe filtrate is stirred into a mixture of 400 g of ice and 900 ml of water
  4. customweakly acid reaction to litmus paper), and
  5. extractionextracted repeatedly with ethyl acetate

Sources & evidence

ORD record
ord-ed9bae4e282e425c89c0abc1f82c5f9d
Source dataset
uspto-grants-1996_11
Patent number
US05578667

Reaction notes

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