Dimethyl Sulfoxide → 2-(4-Dodecyloxyphenyl)benzothiazole

HRID 1243265Notes

Reaction equation

HRID 1243265 reaction equation
[CH2:1]([O:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[SH:29].CS(C)=O>O>[CH2:1]([O:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]2[S:29][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[N:22]=2)=[CH:16][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 87132-AminothiophenolHCID 141069p-Dodecyloxybenzaldehyde

Product 1

HCID 219245262-(4-Dodecyloxyphenyl)benzothiazoleYield 45.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-dodecyloxybenzaldehyde (37.12 g, 0.128 mol), 2-aminobenzenethiol (16 g, 0.128 mol) and dimethylsulfoxide acid (200 cm3) was heated under reflux for 24 hours. The cooled solution was added to water and extracted into dichloromethane (3×50 cm3). The combined organic layers were dried (MgSO4), filtered and the filtrate evaporated down under reduced pressure. The solid residue was recrystallised from ethanol to give 23.1 g (45.7%) of the desired product.

Workup

  1. temperatureunder reflux for 24 hours
  2. extractionextracted into dichloromethane (3×50 cm3)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. customthe filtrate evaporated down under reduced pressure
  6. customThe solid residue was recrystallised from ethanol

Sources & evidence

ORD record
ord-4e5adce4381b4a1ca4217d7503f169db
Source dataset
uspto-grants-2006_10
Patent number
US07118787B2

Reaction notes

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