4-Toluenesulfonyl chloride → HCID 18703635, compound

HRID 2287990Notes

Reaction equation

HRID 2287990 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].O[CH2:13][CH2:14][CH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](=[O:24])[NH:16]1>C(Cl)Cl>[S:1]([CH2:13][CH2:14][CH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17](=[O:24])[NH:16]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 18703633HCID 18703633, compound

Product 1

HCID 18703635HCID 18703635, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tosyl chloride (3.4 g, 17.7 mmol) is added to a solution of TEA (5.1 g, 50.8 mmol) and 1,3-dihydro-3-(2-hydroxyethyl)-2H-isoindol-1-one (3.0 g, 16.9 mmol) in 50 mL of CH2Cl2 at room temperature under argon. After 12 hours, the reaction mixture is extracted with H2O (2×100 mL) and dried over Na2SO4. Evaporation of the solvent gives 4.2 g (75% yield) of 1,3-dihydro-3-(2-tosylethyl)-2H-isoindol-1-one; mp=146-149° C. (dec) after recrystallization from ethyl acetate.

Workup

  1. extractionthe reaction mixture is extracted with H2O (2×100 mL)
  2. dry with materialdried over Na2SO4
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-567308c8a27144368340a95bd5253e9d
Source dataset
uspto-grants-2000_07
Patent number
US06087364

Reaction notes

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