Potassium Carbonate → HCID 67079238, compound

HRID 2194332Notes

Reaction equation

HRID 2194332 reaction equation
[Cl: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([C:21]2[N:25]=[C:24](S(C3C=CC(C)=CC=3)(=O)=O)[S:23][N:22]=2)[CH2:20][CH2:19]1>C(#N)C>[Cl:1][C:2]1[CH:8]=[C:7]([O:9][C:24]2[S:23][N:22]=[C:21]([C:18]3([Cl:17])[CH2:20][CH2:19]3)[N:25]=2)[C:6]([CH3:10])=[CH:5][C:3]=1[NH2:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 220610464-Amino-5-chloro-2-methylphenolHCID 67079770HCID 67079770, compound

Product 1

HCID 67079238HCID 67079238, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3.00 g (19.04 mmol) of 2-chloro-4-hydroxy-5-methylaniline are introduced into 50 ml of acetonitrile, treated at ambient temperature with 3.16 g (22.84 mmol) of potassium carbonate and stirred at ambient temperature for 30 min. Subsequently, 6.26 g (19.04 mmol) of 3-(1-chlorocyclopropyl)-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 on a rotary evaporator, the residue is taken up in dichloromethane and the solution is extracted twice with water, dried over Na2SO4 and freed from solvent under vacuum. The residue is purified by column chromatography. 3.18 g of product are obtained (93.3% purity, 49.4% yield, log P (pH 2.3)=3.50).

Workup

  1. stirringthe reaction mixture is stirred at 50° C. for 12 h
  2. temperatureAfter cooling
  3. concentrationthe mixture is concentrated on a rotary evaporator
  4. extractionthe solution is extracted twice with water
  5. dry with materialdried over Na2SO4
  6. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-7b5134aa89a54d4288d12bc59f60204f
Source dataset
uspto-grants-2012_12
Patent number
US08334235B2

Reaction notes

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