Potassium Carbonate → HCID 67080862, compound

HRID 389833Notes

Reaction equation

HRID 389833 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([OH:9])[C:6]([CH3:10])=[CH:5][C:3]=1[NH2:4].C(=O)([O-])[O-].[K+].[K+].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2([C:27]3[N:31]=[C:30](S(C4C=CC(C)=CC=4)(=O)=O)[S:29][N:28]=3)[CH2:26][CH2:25]2)=[CH:20][CH:19]=1>C(#N)C>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2([C:27]3[N:31]=[C:30]([O:9][C:7]4[C:6]([CH3:10])=[CH:5][C:3]([NH2:4])=[C:2]([CH3:1])[CH:8]=4)[S:29][N:28]=3)[CH2:26][CH2:25]2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 765444-Amino-2,5-dimethylphenolHCID 67080890HCID 67080890, compound

Product 1

HCID 67080862HCID 67080862, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.70 g (5.12 mmol) of 2,5-dimethyl-4-hydroxyaniline is placed in 18 ml of acetonitrile, 0.85 g (6.14 mmol) of potassium carbonate is added at ambient temperature and the mixture is stirred at ambient temperature for 30 min. Subsequently, 2.0 g (5.12 mmol) of 3-[1-(4-chloro-phenyl)cyclopropyl]-5-[(4-methylphenyl)sulphonyl]-1,2,4-thiadiazole are added and the reaction mixture is stirred at 50° C. for 12 h. After cooling, the reaction mixture is concentrated using a rotary evaporator and the residue is taken up in dichloromethane, extracted twice with water, dried over Na2SO4 and freed from the solvent under vacuum. 1.46 g of clean product are obtained (76.9% yield, log P (pH 2.3)=4.44).

Workup

  1. stirringthe reaction mixture is stirred at 50° C. for 12 h
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture is concentrated
  4. customa rotary evaporator
  5. extractionextracted twice with water
  6. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-e724a805fded4ed7a021e59b31093647
Source dataset
uspto-grants-2013_02
Patent number
US08383139B2

Reaction notes

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