Water → HCID 16662057, compound

HRID 2382509Notes

Reaction equation

HRID 2382509 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.N1C=CC=CC=1.[NH:19]([CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CC(OC)(C)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 74014-Methoxybenzenesulfonyl chlorideHCID 2367962-(2-Anilinoethyl)pyridine

Product 1

HCID 16662057HCID 16662057, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

To a 25 ml round bottom flask, 0.21 g 4-methoxybenzenesulfonyl chloride and 0.08 mL of pyridine were dissolved in 10 ml of MTBE. To this solution was added 0.2 g of 2-(2-anilinoethyl)pyridine. The reaction was heated at reflux for one hour and then let cool down to room temperature. To the reaction was added 10 mL of water. The organic layer was separated and washed with 10 mL of water. The organic layer was dried over MgSO4, filtered, and concentrated to yield a brown oil. The oil was purified on silica gel to recover 0.3 g of a tanned solid with the following spectroscopic properties:

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for one hour
  3. customThe organic layer was separated
  4. washwashed with 10 mL of water
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield a brown oil
  9. customThe oil was purified on silica gel
  10. customto recover 0.3 g of a tanned solid with the following spectroscopic properties

Sources & evidence

ORD record
ord-5ca91c8716514243ad60e645348ba9d1
Source dataset
uspto-grants-2012_09
Patent number
US08263046B2

Reaction notes

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