Potassium Iodide → 4,6-Diphenyl-2-(5-chloro-4-hexyloxy-2-hydroxyphenyl)-s-triazine

HRID 1488842Notes

Reaction equation

HRID 1488842 reaction equation
[Cl:1][C:2]1[C:3]([OH:27])=[CH:4][C:5]([OH:26])=[C:6]([C:8]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11]=[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:9]=2)[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]>C(OCCO)C>[C:14]1([C:12]2[N:11]=[C:10]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:9]=[C:8]([C:6]3[CH:7]=[C:2]([Cl:1])[C:3]([O:27][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])=[CH:4][C:5]=3[OH:26])[N:13]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 81011-BromohexaneHCID 11430Potassium CarbonateHCID 1358435932-(5-Chloro-2,4-dihydroxyphenyl)-4,6-diphenyl-s-triazine

Product 1

HCID 1358436004,6-Diphenyl-2-(5-chloro-4-hexyloxy-2-hydroxyphenyl)-s-triazine

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Conditions

Temperature
110 °C

Procedure

To a 350 mL sulfonation flask equipped with a mechanical stirrer, condenser, dropping funnel and a nitrogen atmosphere are charged 26.3 g (70 mmol) of the product of Example 54, 10.6 g (77 mmol) of potassium carbonate, 50 mg of potassium iodide, and 50 mL of 2-ethoxyethanol. The suspension is warmed to 110° C., and 10.8 g (77 mmol) of 1-bromohexane are added dropwise over 30 minutes. After 8 hours, the reaction mixture is cooled to room temperature, the precipitate is removed by filtration, washed with water to pH 6, rinsed with methanol and dried at 70° C. under vacuum. The crude beige product (26.9 g) is recrystallized twice from 600 mL of 2-ethoxyethanol to give the title compound in a yield of 18.6 g as a yellow solid melting at 147°-149° C., purity 98.7% (DSC assay).

Workup

  1. customTo a 350 mL sulfonation flask equipped with a mechanical stirrer, condenser
  2. temperaturethe reaction mixture is cooled to room temperature
  3. customthe precipitate is removed by filtration
  4. washwashed with water to pH 6
  5. washrinsed with methanol
  6. customdried at 70° C. under vacuum
  7. customThe crude beige product (26.9 g) is recrystallized twice from 600 mL of 2-ethoxyethanol

Sources & evidence

ORD record
ord-390f6eb243434359bf23cdffdb432608
Source dataset
uspto-grants-1997_10
Patent number
US05675004

Reaction notes

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