Methanesulfonyl chloride → 4-Methanesulfonamidophthalimide

HRID 353046Notes

Reaction equation

HRID 353046 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:8]=[C:9]2[C:14](=[O:15])[NH:13][C:11](=[O:12])[C:10]2=[CH:16][CH:17]=1>N1C=CC=CC=1>[CH3:1][S:2]([NH:6][C:7]1[CH:8]=[C:9]2[C:14](=[O:15])[NH:13][C:11](=[O:12])[C:10]2=[CH:16][CH:17]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 729154-Aminophthalimide

Product 1

HCID 9750204-MethanesulfonamidophthalimideYield 76.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulfonylchloride (2.6 ml, 0.034 mol) was added dropwise to a stirred suspension of 4-aminophthalimide (5.0 g, 0.031 mol) in pyridine (50 ml). The mixture was stirred for 48 h under N2 at room temperature, after which time the solid formed was isolated by filtration, washing well with H2O and CH2Cl2 and then dried in vacuo to afford the subtitle compound as a colourless solid (5.67 g, 76%). Rf 0.52 (CH2Cl2/MeOH/0.88NH3 90/10/1, v/v). MS m/z 241 (MH+).

Workup

  1. customafter which time the solid formed
  2. customwas isolated by filtration
  3. washwashing well with H2O and CH2Cl2
  4. customdried in vacuo

Sources & evidence

ORD record
ord-4d751eec7c3345618cadd334cf0e2e27
Source dataset
uspto-grants-2004_06
Patent number
US06750214B2

Reaction notes

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