Cesium carbonate → HCID 86615559, compound

HRID 605220Notes

Reaction equation

HRID 605220 reaction equation
[Br:1][C:2]1[S:6][C:5]([NH:7][C:8](=[O:19])[C:9]2[CH:14]=[CH:13][C:12](Cl)=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=2)=[N:4][CH:3]=1.[SH:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[Br:1][C:2]1[S:6][C:5]([NH:7][C:8](=[O:19])[C:9]2[CH:14]=[CH:13][C:12]([S:20][C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=3)=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=2)=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 2401474-MercaptophenolHCID 54918044HCID 54918044, compound

Product 1

HCID 86615559HCID 86615559, compoundYield 111.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of the product of Example 202A (300 mg, 0.8274 mmol) in anhydrous N,N-dimethylformamide (8 mL) was treated with 4-mercaptophenol (104.4 mg, 0.8274 mmol) and cesium carbonate (539 mg, 1.655 mmol) at room temperature, then heated at 100° C. under a nitrogen atmosphere for 2 hours. The reaction was cooled to room temperature and the solvent removed by rotary evaporation in vacuo. The residue was taken up in water (50 mL) and the pH adjusted to 3 with 1N aqueous HCl. The aqueous was extracted with ethyl acetate (100 mL), and the organic extract washed with water (2×25 mL) and brine (25 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation to give the product as a golden-brown solid (416 mg, 111%).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customthe solvent removed by rotary evaporation in vacuo
  3. extractionThe aqueous was extracted with ethyl acetate (100 mL)
  4. extractionthe organic extract
  5. washwashed with water (2×25 mL) and brine (25 mL)
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-83ad47e2ad4e4a3e979d6f01a4c4051b
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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