4-Toluenesulfonyl chloride → HCID 19849033, compound

HRID 1608276Notes

Reaction equation

HRID 1608276 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:7][S:6][C:5]2([CH2:11][CH2:10][CH:9]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:8]2)[O:4]1.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>N1C=CC=CC=1.CCOCC>[CH3:28][C:18]1[CH:23]=[CH:22][C:21]([S:24]([O:1][CH2:2][CH:3]2[CH2:7][S:6][C:5]3([CH2:11][CH2:10][CH:9]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:8]3)[O:4]2)(=[O:26])=[O:25])=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 19849031HCID 19849031, compound

Product 1

HCID 19849033HCID 19849033, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

To a cold stirred solution of the product of Example O (2.60 g, 10 mmol) in pyridine (30 ml) is added p-toluenesulfonyl chloride (1.91 g, 10 mmol) in portions over 15 minutes. When the addition is completed the reaction is stirred at room temperature for 2 hrs. The reaction mixture is diluted with ether and washed with water, 0.5N aqueous sodium bisulfate solution, 5% aqueous sodium bicarbonate solution and water. The organic layer is dried over sodium sulfate, filtered, and the filtrate is concentrated on a rotary evaporator to give the titled compound.

Workup

  1. additionWhen the addition
  2. washwashed with water, 0.5N aqueous sodium bisulfate solution, 5% aqueous sodium bicarbonate solution and water
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-b50a0229a3c64aecaf07960678688e56
Source dataset
uspto-grants-1989_09
Patent number
US04870098

Reaction notes

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