Water → HCID 1582610, compound

HRID 2295524Notes

Reaction equation

HRID 2295524 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.C(N(CC)CC)C.O>ClCCl>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([O:1][N:2]2[C:3](=[O:12])[C:4]3=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]3[C:6]2=[O:7])(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 10665N-Hydroxyphthalimide

Product 1

HCID 1582610HCID 1582610, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

In a 3-neck, 500 ml round bottom flask, dichloromethane (100 ml) was added to 16.3 g (0.10 mole) of N-hydroxyphthalimide. To this was added 21.1 g (0.10 mole) of 4-chlorobenzenesulfonyl chloride. To this suspension at ice-bath temperature, with slow stirring, was added dropwise 10.1 g (0.10 mole) of triethylamine in 50 ml of dichloromethane. This stirred reaction mixture was held at ambient temperature for 72 hours. Then, more dichloromethane and 100 ml of water were added to the suspension. The dichloromethane extract was dried with magnesium sulfate. Solvent was removed under reduced pressure and the residue was recrystallized from 500 ml of ethyl acetate to give 10.2 g of a white solid, mp 178°-180° C.

Workup

  1. customThis stirred reaction mixture
  2. extractionThe dichloromethane extract
  3. dry with materialwas dried with magnesium sulfate
  4. customSolvent was removed under reduced pressure
  5. customthe residue was recrystallized from 500 ml of ethyl acetate

Sources & evidence

ORD record
ord-490a8880ee29480f843a674c7b670912
Source dataset
uspto-grants-1984_01
Patent number
US04425424

Reaction notes

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