Potassium Iodide → HCID 178442339, compound

HRID 1979062Notes

Reaction equation

HRID 1979062 reaction equation
C(C1C=CC([C:11]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:19][CH:18]=3)[N:14]=[C:13]([C:27]3[CH:32]=[C:31]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[C:30]([OH:39])=[CH:29][C:28]=3[OH:40])[N:12]=2)=CC=1)(C)(C)C.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:50][C:51]([O:53][CH2:54][CH3:55])=[O:52]>CC(C)=O>[C:23]([C:20]1[CH:19]=[CH:18][C:17]([C:15]2[NH:14][C:13]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:19][CH:18]=3)([C:27]3[CH:32]=[C:31]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[C:30]([O:39][CH2:50][C:51]([O:53][CH2:54][CH3:55])=[O:52])=[CH:29][C:28]=3[OH:40])[N:12]=[CH:11][N:16]=2)=[CH:22][CH:21]=1)([CH3:24])([CH3:25])[CH3:26]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 135804512HCID 135804512, compound

Product 1

HCID 178442339HCID 178442339, compoundYield 171.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred mixture of 10 g of 2,4-bis(4-tert-butylphenyl)-6-(2,4-dihydroxy-5-hexylphenyl)-1,3,5-triazine, 7.4 g of anhydrous potassium carbonate, 0.5 g of potassium iodide, and 80 mL of acetone was added 2.2 mL (2.5 g) of ethyl chloroacetate. The mixture was stirred at reflux for 2.5 h and then allowed to cool to room temperature. The solids were removed by filtration and washed with methylene chloride. The combined filtrates were concentrated under reduced pressure to a volume of 75 mL and diluted with 50 mL of methanol. The resulting solid was collected by filtration and washed with methanol. After drying in vacuo, 10 g of 2,6-bis(4-tert-butylphenyl)-6-(2-hydroxy-4-ethoxycarbonylmethoxy-5-hexylphenyl)-1,3,5-triazine was obtained. The structure was verified by 1HNMR spectroscopy.

Workup

  1. temperatureat reflux for 2.5 h
  2. customThe solids were removed by filtration
  3. washwashed with methylene chloride
  4. concentrationThe combined filtrates were concentrated under reduced pressure to a volume of 75 mL
  5. additiondiluted with 50 mL of methanol
  6. filtrationThe resulting solid was collected by filtration
  7. washwashed with methanol
  8. customAfter drying in vacuo

Sources & evidence

ORD record
ord-b1840aef2a8e4406bc286b496c742780
Source dataset
uspto-grants-2001_05
Patent number
US06239276B1

Reaction notes

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