4-Toluenesulfonyl chloride → HCID 23331013, compound

HRID 224535Notes

Reaction equation

HRID 224535 reaction equation
[CH2:1]([NH:4][C:5](=[O:14])[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[Cl:13])[CH:2]=[CH2:3].[H-].[Na+].[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>O1CCCC1>[CH2:1]([N:4]([C:5](=[O:14])[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[Cl:13])[S:23]([C:20]1[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=1)(=[O:25])=[O:24])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 1591522HCID 1591522, compound

Product 1

HCID 23331013HCID 23331013, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.6 g (0.02 mole) of N-allyl-2,4-dichlorobenzamide was added to 1.2 g (0.024 mole) of 50% sodium hydride in 20 ml of dry tetrahydrofuran. The mixture was stirred at room temperature for 30 minutes to react them. Then, 4.2 g (0.024 mole) of p-toluenesulfonyl chloride was added, and reacted at room temperature for 1 hour. The tetrahydrofuran was distilled off under reduced pressure. After adding cold water to the residual oil, it was extracted with benzene, dried over anhydrous magnesium sulfate, and concentrated to afford an oily substance. It was purified by silica gel chromatography to afford compound No. 42 shown in Table 2 in a yield of 68%. Its refractive index and elemental analysis values are also shown in Table 2.

Workup

  1. customto react them
  2. customreacted at room temperature for 1 hour
  3. distillationThe tetrahydrofuran was distilled off under reduced pressure
  4. additionAfter adding cold water to the residual oil, it
  5. extractionwas extracted with benzene
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customto afford an oily substance
  9. customIt was purified by silica gel chromatography
  10. customto afford compound No

Sources & evidence

ORD record
ord-b0aa6f071b40435aad1db104603f36e1
Source dataset
uspto-grants-1980_11
Patent number
US04233061

Reaction notes

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