Hydrochloric Acid → 6-{4-[6-(4-Nonylphenyl)benzothiazol-2-yl]phenoxy}hexan-1-ol

HRID 1243269Notes

Reaction equation

HRID 1243269 reaction equation
[OH-].[Na+].[CH2:3]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:33]=[CH:32][C:21]3[N:22]=[C:23]([C:25]4[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=4)[S:24][C:20]=3[CH:19]=2)=[CH:14][CH:13]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].Br[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][OH:41].[I-].[K+].Cl>O.CO>[CH2:3]([C:12]1[CH:13]=[CH:14][C:15]([C:18]2[CH:33]=[CH:32][C:21]3[N:22]=[C:23]([C:25]4[CH:30]=[CH:29][C:28]([O:31][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][OH:41])=[CH:27][CH:26]=4)[S:24][C:20]=3[CH:19]=2)=[CH:16][CH:17]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 14798Sodium HydroxideHCID 779706-Bromo-1-hexanolHCID 1357617792-(4-Hydroxyphenyl)-6-(4-nonylphenyl)benzothiazole

Product 1

HCID 219245276-{4-[6-(4-Nonylphenyl)benzothiazol-2-yl]phenoxy}hexan-1-olYield 62%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of sodium hydroxide (0.08 g, 0.0020 mol) in water (20 cm3) was added dropwise to a solution of 4-[6-(4-nonylphenyl)benzothiazol-2yl]phenol (0.42 g, 0.0010 mol) in methanol (50 cm3). The 6-bromohexanol (0.18 g, 0.001 mol) was then added dropwise, followed by the potassium iodide (0.02 g, 0.00125 mol) in one portion. The reaction mixture was heated under reflux overnight and the poured onto a mixture of water (100 cm3) and 10% hydrochloric acid (20 cm3). The resultant precipitate was filtered off and recrystallised from ethanol to yield 0.31 g (62%) of the pure compound.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux overnight
  3. filtrationThe resultant precipitate was filtered off
  4. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-209622e8617c4fd7a94c296cb565df7a
Source dataset
uspto-grants-2006_10
Patent number
US07118787B2

Reaction notes

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