p-Toluenesulfonic acid → N,N-diethyl-4-(thiazol-2-yl)aniline

HRID 56110

Reaction equation

HRID 56110 reaction equation
[CH2:1]([N:3]([CH2:13][CH3:14])[C:4]1[CH:12]=[CH:11][C:7]([C:8](=[S:10])[NH2:9])=[CH:6][CH:5]=1)[CH3:2].Br[CH2:16][CH:17](OC)OC.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCO>[CH2:13]([N:3]([CH2:1][CH3:2])[C:4]1[CH:12]=[CH:11][C:7]([C:8]2[S:10][CH:16]=[CH:17][N:9]=2)=[CH:6][CH:5]=1)[CH3:14]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 816722-Bromo-1,1-dimethoxyethaneHCID 28410527Benzenecarbothioamide, 4-(diethylamino)-

Product 1

HCID 20471151N,N-diethyl-4-(thiazol-2-yl)anilineYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 4-(diethylamino)benzothioamide (2.29 g, 11 mmol) in EtOH (60 mL) were added 2-bromo-1,1-dimethoxyethane (1.86 g, 11 mmol) and p-toluenesulfonic acid (1.89 g, 11 mmol). The reaction mixture was heated at 95° C. overnight, then cooled to rt and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc/Et3N (V/V/V)=2:1:0.05) to give the title compound as a white solid (1.40 g, 55%).

Workup

  1. temperaturecooled to rt
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by a silica gel column chromatography (PE/EtOAc/Et3N (V/V/V)=2:1:0.05)

Sources & evidence

ORD record
ord-ac4c8fb978c34e78bf800f3165254691
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Linked notes

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