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

HRID 132552Notes

Reaction equation

HRID 132552 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) 61.70 (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-ecad87297ef84186ac538b4dac0ff9a7
Source dataset
uspto-grants-2008_06
Patent number
US07388013B2

Reaction notes

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