Potassium Carbonate → {4-[(1,3-Benzothiazol-2-yl)sulfanyl]phenyl}(2,5-dichlorophenyl)methanone

HRID 1442461Notes

Reaction equation

HRID 1442461 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9](F)=[CH:8][CH:7]=1)=[O:5].[S:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[N:20]=[C:19]1[SH:27].C(=O)([O-])[O-].[K+].[K+]>O>[Cl:1][C:2]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([S:27][C:19]2[S:18][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[N:20]=2)=[CH:8][CH:7]=1)=[O:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 120399992,5-dichloro-4'-fluorobenzophenonHCID 178418395HCID 178418395, compound

Product 1

HCID 59165205{4-[(1,3-Benzothiazol-2-yl)sulfanyl]phenyl}(2,5-dichlorophenyl)methanoneYield 78.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

269.1 g (1.000 mol) of 2,5-dichloro-4′-fluorobenzophenon, 175.6 g (1.050 mol) of 2-benzothiazolethiol, 152.0 g (1.100 mol) of potassium carbonate, and 1.500 ml of N,N′-dimethylacetamide were added into a 3 L three-necked flask equipped with a stirrer, thermometer, cooling pipe, and nitrogen inlet tube, and dehydrated. The reaction solution was heated by use of an oil bath and was allowed to react at 110 degrees C. in a nitrogen atmosphere for 2 hours. After the disappearance of material was confirmed by a thin layer chromatography, the mixture was cooled to ambient temperature. Then, the reaction solution was gradually poured into 3 L of water to cause coagulation. The resulting product by filtration was dissolved into 4 L of toluene. The organic layer was washed by brine to be neutral. After the organic layer was dried by magnesium sulfate, the solvent was removed by an evaporator. The rough yield was 350.3 g. By using 1.5 L of toluene heated at 80 degrees C., the dried product was recrystallized for isolation to obtain 325.4 g of the refining material in 78.2% yield.

Workup

  1. customequipped with a stirrer
  2. temperaturethermometer, cooling pipe, and nitrogen inlet tube
  3. temperatureThe reaction solution was heated by use of an oil bath
  4. customto react at 110 degrees C
  5. filtrationThe resulting product by filtration
  6. dissolutionwas dissolved into 4 L of toluene
  7. washThe organic layer was washed by brine
  8. dry with materialAfter the organic layer was dried by magnesium sulfate
  9. customthe solvent was removed by an evaporator
  10. temperatureheated at 80 degrees C
  11. custom, the dried product was recrystallized for isolation

Sources & evidence

ORD record
ord-a522779aca314438b0b3bd36ae968c77
Source dataset
uspto-grants-2010_02
Patent number
US07658867B2

Reaction notes

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