Potassium Carbonate → HCID 67238087, compound

HRID 2194335Notes

Reaction equation

HRID 2194335 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[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]2[N:30]=[C:29](S(C3C=CC(C)=CC=3)(=O)=O)[S:28][N:27]=2)=[CH:20][CH:19]=1>C(#N)C>[Cl:1][C:2]1[CH:8]=[C:7]([O:9][C:29]2[S:28][N:27]=[C:26]([CH2:25][CH2:24][C:21]3[CH:22]=[CH:23][C:18]([Cl:17])=[CH:19][CH:20]=3)[N:30]=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 67079865HCID 67079865, compound

Product 1

HCID 67238087HCID 67238087, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.45 g (9.24 mmol) of 2-chloro-4-hydroxy-5-methylaniline are introduced into 18 ml of acetonitrile, treated with 1.53 g (11.08 mmol) of potassium carbonate at ambient temperature and stirred at ambient temperature for 30 min. Subsequently, 3.50 g (9.24 mmol) of 3-[2-(4-chlorophenyl)ethyl]-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 the solvent under vacuum. 3.11 g of product are obtained (94.3% purity, 83.4% yield, log P (pH 2.3)=4.50).

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

Sources & evidence

ORD record
ord-e4630e1c01874fd5bd022dc01560ef32
Source dataset
uspto-grants-2012_12
Patent number
US08334235B2

Reaction notes

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