Toluene → HCID 23302451, compound

HRID 1953287Notes

Reaction equation

HRID 1953287 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10][C:11]3[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=3)=[N:7][C:6]=2[CH:19]=1.[C:20]1([CH3:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1OB(O)O>O.CO.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10][C:11]3[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=3)=[N:7][C:6]=2[CH:19]=1

Participants

9

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 13862916Tolylboric acidHCID 23302440HCID 23302440, compound

Product 1

HCID 23302451HCID 23302451, compound

Reagents, catalysts & solvents 4

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under a nitrogen atmosphere 1.3 g (3.95 mmol) of 4-[(5-bromobenzothiazol-2-yl)-methyl]-benzonitrile and 1.3 g (1.1 mmol) of bis(triphenylphosphine)-palladium(II)-chloride are stirred into 40 ml toluene for 15 minutes at 40° C. Then 1.3 g (12.3 mmol) of sodium carbonate in 5.6 ml water and 0.84 g (6.1 mmol) of o-tolylboric acid in 5 ml methanol are added. The reaction mixture is refluxed for 10 hours. After cooling the reaction solution is diluted with ethyl acetate and extracted with water. The combined organic extracts are washed with sodium chloride solution and dried. The residue is chromatographed on silica gel and eluted with ethyl acetate/petroleum ether 5:95, 10:95 and 15:85. The desired fractions are combined and concentrated by evaporation.

Workup

  1. temperatureThe reaction mixture is refluxed for 10 hours
  2. temperatureAfter cooling the reaction solution
  3. extractionextracted with water
  4. washThe combined organic extracts are washed with sodium chloride solution
  5. customdried
  6. customThe residue is chromatographed on silica gel
  7. washeluted with ethyl acetate/petroleum ether 5:95, 10:95 and 15:85
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-40f776de783044809deda5ae084b60bc
Source dataset
uspto-grants-2000_09
Patent number
US06114532

Reaction notes

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