4-Toluenesulfonyl chloride → HCID 53673877, compound

HRID 223677Notes

Reaction equation

HRID 223677 reaction equation
[CH:1]([O:5][C:6](=[O:16])[CH2:7][CH:8]([CH3:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14])([CH2:3][CH3:4])[CH3:2].[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>N1C=CC=CC=1>[CH:1]([O:5][C:6](=[O:16])[CH2:7][CH:8]([CH3:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][S:23]([C:20]1[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=1)(=[O:25])=[O:24])([CH2:3][CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 54465344HCID 54465344, compound

Product 1

HCID 53673877HCID 53673877, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of the oily ester, thus obtained, one ml of pyridine and 485 mg of p-toluenesulphonyl chloride was stirred at room temperature for 16 hours. The reaction mixture was poured into ice-water, extracted with ethyl acetate, the extract washed with dilute sulphuric acid, a saturated aqueous solution of sodium bicarbonate, a saturated aqueous solution of sodium chloride, dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of methylene chloride and ethyl acetate (20:1) as eluent to give 647 mg of the subtitle compound having the following physical characteristics:

Workup

  1. customthus obtained
  2. extractionextracted with ethyl acetate
  3. washthe extract washed with dilute sulphuric acid
  4. dry with materiala saturated aqueous solution of sodium bicarbonate, a saturated aqueous solution of sodium chloride, dried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel using
  7. additiona mixture of methylene chloride and ethyl acetate (20:1) as eluent

Sources & evidence

ORD record
ord-e5b4c231eef14a26ac58d5d1b86d8587
Source dataset
uspto-grants-1982_10
Patent number
US04355170

Reaction notes

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