Potassium Iodide → HCID 135800027, compound

HRID 2294671Notes

Reaction equation

HRID 2294671 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)[N:12]=[C:11]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=2)[N:10]=1.Br[C:32]1[CH:33]=[C:34](OC)[CH:35]=[CH:36][CH:37]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].BrCCCCCC>C(OCCO)C>[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:34][CH2:33][CH2:32][CH2:37][CH2:36][CH3:35])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)[N:12]=[C:11]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=2)[N:10]=1

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 81011-BromohexaneHCID 11430Potassium CarbonateHCID 169713-BromoanisoleHCID 135800029HCID 135800029, compound

Product 1

HCID 135800027HCID 135800027, compound

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

10 g (0.025 mol) of 2-(2,4-dihydroxyphenyl)-4,6-bis(3-methoxyphenyl)-1,3,5-triazine (prepared by the method of Example 8 starting from 3-bromoanisole), 3.8 g of potassium carbonate and 30 mg of potassium iodide are heated in 25 ml of 2-ethoxyethanol at 110 C. for one hour, followed by dropwise addition of 6.7 g (0.041 mol) of 1-bromohexane and stirring at 110 C. for a further 32 hours. After cooling, the mixture is filtered, the solid material is washed neutral with water and then washed with methanol and dried. The crude product is purified by column chromatography (250 g SiO2 35-70 μm; eluent toluene/petroleum ether 1:1). This gives the compound of formula ##STR24##

Workup

  1. waitfor a further 32 hours
  2. temperatureAfter cooling
  3. filtrationthe mixture is filtered
  4. washthe solid material is washed neutral with water
  5. washwashed with methanol
  6. customdried
  7. customThe crude product is purified by column chromatography (250 g SiO2 35-70 μm; eluent toluene/petroleum ether 1:1)
  8. customThis gives the compound of formula

Sources & evidence

ORD record
ord-4676a870e23c460485d6408ba6284c77
Source dataset
uspto-grants-1997_11
Patent number
US05688995

Reaction notes

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