Potassium Carbonate → HCID 67080809, compound

HRID 389829Notes

Reaction equation

HRID 389829 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:19]=[C:20]([CH:37]=[CH:38][CH:39]=1)[CH2:21][C:22]1[N:26]=[C:25](S(C2C=CC(C)=CC=2)(=O)=O)[S:24][N:23]=1>C(#N)C>[Cl:17][C:18]1[CH:19]=[C:20]([CH:37]=[CH:38][CH:39]=1)[CH2:21][C:22]1[N:26]=[C:25]([O:9][C:7]2[C:6]([CH3:10])=[CH:5][C:3]([NH2:4])=[C:2]([CH3:1])[CH:8]=2)[S:24][N:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 765444-Amino-2,5-dimethylphenolHCID 670808063-(3-Chlorobenzyl)-5-[(4-methylphenyl)sulphonyl]-1,2,4-thiadiazole

Product 1

HCID 67080809HCID 67080809, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3.86 g (28.1 mmol) of 2,5-dimethyl-4-hydroxyaniline are placed in 50 ml of acetonitrile, 4.66 g (33.8 mmol) of potassium carbonate are added at ambient temperature and the mixture is stirred for 30 min at ambient temperature. Subsequently, 11.0 g (28.1 mmol) of 3-(3-chlorobenzyl)-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 mixture is concentrated using a rotary evaporator and the residue is taken in dichloromethane, extracted twice with water, dried over Na2SO4 and freed from the solvent under vacuum. 6.86 g of product are obtained (96.4% purity, 68.0% yield, log P (pH 2.3)=3.68).

Workup

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

Sources & evidence

ORD record
ord-ec64cd2ea29f48b097c0bb26bc528ff9
Source dataset
uspto-grants-2013_02
Patent number
US08383139B2

Reaction notes

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