4-Toluenesulfonyl chloride → HCID 18703634, compound

HRID 2287993Notes

Reaction equation

HRID 2287993 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:12][N:13]1[CH:21]([CH2:22][CH2:23]O)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]1=[O:25]>C(Cl)Cl>[CH3:12][N:13]1[CH:21]([CH2:22][CH2:23][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]1=[O:25]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 12609442HCID 12609442, compound

Product 1

HCID 18703634HCID 18703634, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

p-Toluene sulfonyl chloride (2.3 g, 12.1 mmol) is added to a solution of TEA (3.5 g, 34.5 mmol) and 1,3-dihydro-2-methyl-3-(2-hydroxyethyl)-2H-isoindol-1-one (2.2 g, 11.5 mmol) in 50 mL of CH2Cl2 at room temperature under argon. The mixture is stirred at room temperature overnight and washed with water (3×50 mL). The organic layer is dried over Na2SO4 and evaporated to give an oil which is chromatographed in ethyl acetate over silica gel to give 1.5 g (38% yield) of 1,3-dihydro-2-methyl-3-(2-tosylethyl)-2H-isoindol-1-one.

Workup

  1. washwashed with water (3×50 mL)
  2. dry with materialThe organic layer is dried over Na2SO4
  3. customevaporated
  4. customto give an oil which
  5. customis chromatographed in ethyl acetate over silica gel

Sources & evidence

ORD record
ord-5d9b98abc573416dbe779b900b8ae56b
Source dataset
uspto-grants-2000_07
Patent number
US06087364

Reaction notes

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