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

HRID 1946224Notes

Reaction equation

HRID 1946224 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>C1(C)C=CC=CC=1>[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

6

Reactant 4

HCID 962WaterHCID 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 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A charge of 269.1 g (1.00 mol) of 2,5-dichloro-4′-fluorobenzophenone, 175.6 g (1.05 mol) of 2-benzothiazolethiol, 152.0 g (1.10 mol) of potassium carbonate and 1.5 L of dehydrated N,N′-dimethylacetamide was weighed into a 3 L three-neck flask equipped with a stirrer, a thermometer, a cooling tube and a nitrogen gas introducing tube. The reaction solution was heated under nitrogen atmosphere to 110° C. for 2 hours using an oil bath. After the disappearance of raw materials was confirmed by thin layer chromatography, the reaction solution was left to cool to room temperature. The reaction solution was then gradually added to 3 L of water to coagulate a product, which was filtered. The product obtained by filtration was dissolved in 4 L of toluene. The organic layer was washed with brine until an aqueous layer became neutral. After the organic layer was dried over magnesium sulfate, the solvent was removed by an evaporator. A crude yield was 350.3 g. A 1.5 L aliquot of toluene heated to 80° C. was used for recrystallization to yield 325.4 g (0.782 mol) of a purified product in 78.2% yield.

Workup

  1. customwas weighed into a 3 L three-neck flask
  2. customequipped with a stirrer
  3. additiona thermometer, a cooling tube and a nitrogen gas introducing tube
  4. waitthe reaction solution was left
  5. temperatureto cool to room temperature
  6. filtrationwas filtered
  7. customThe product obtained by filtration
  8. washThe organic layer was washed with brine until an aqueous layer
  9. dry with materialAfter the organic layer was dried over magnesium sulfate
  10. customthe solvent was removed by an evaporator
  11. temperatureA 1.5 L aliquot of toluene heated to 80° C.
  12. customwas used for recrystallization

Sources & evidence

ORD record
ord-0da6ed6fab17453880c2e582f96a6316
Source dataset
uspto-grants-2013_03
Patent number
US08399148B2

Reaction notes

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