Chlorosulfonic acid → 4-[4-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)butyl]benzenesulfonyl chloride

HRID 2220899Notes

Reaction equation

HRID 2220899 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:22][S:23](O)(=[O:25])=[O:24]>>[O:21]=[C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:19](=[O:20])[N:11]1[CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][C:4]([S:23]([Cl:22])(=[O:25])=[O:24])=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 104688312-(4-Phenylbutyl)isoindole-1,3-dione

Product 1

HCID 220544564-[4-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)butyl]benzenesulfonyl chlorideYield 99%

Procedure

2-(4-Phenylbutyl)isoindole-1,3-dione 12 (1.9 g, 6.8 mmol) was added to chlorosulfonic acid (10 mL, 138 mmol) at 0° C. and the mixture was stirred for 1 h at the temperature. After storing in refrigerator at −5° C. overnight, the reaction mixture was poured onto crushed ice (100 g) and precipitates were collected by a suction filtration and dried under high vacuum to afford the desired product 13 (2.48 g, 99% yield). 1H NMR (300 MHz, CDCl3) δ 1.70 (m, 4H), 2.78 (m, 2H), 3.70 (m, 2H), 7.40 (d, 2H) 7.70 (d, 2H), 7.85 (d, 2H), 7.95 (d, 2H).

Workup

  1. waitAfter storing in refrigerator at −5° C. overnight
  2. additionthe reaction mixture was poured
  3. customprecipitates
  4. filtrationwere collected by a suction filtration
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-436b502fe1c54e39b209ba25b1acfbe6
Source dataset
uspto-grants-2008_05
Patent number
US07368447B2

Reaction notes

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