Chlorosulfonic acid → 2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-indan-5-sulfonyl chloride

HRID 2405882Notes

Reaction equation

HRID 2405882 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[N:10]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:20].[Cl:21][S:22](O)(=[O:24])=[O:23]>CC#N.O>[O:20]=[C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18](=[O:19])[N:10]1[CH:2]1[CH2:1][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:22]([Cl:21])(=[O:24])=[O:23])[CH:8]=2)[CH2:3]1

Participants

5

Reactant 2

HCID 24638Chlorosulfonic acidHCID 109998862-(1,3-Isoindolinedion-2-yl)indane

Product 1

HCID 538616392-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-indan-5-sulfonyl chloride

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of compound 747-C (0.72 g, 2.7 mmol) in MeCN (50 mL) was added chlorosulfonic acid (3.72 g, 32.4 mmol), drop-wise, and the reaction mixture was stirred at ambient temperature for 48 h. The reaction mixture was diluted with H2O, extracted with CH2Cl2, dried over Na2SO4, filtered, and dried to afford 0.976 g of compound 747-D as a brown solid. 1H-NMR (CDCl3) δ 3.26-3.43 (m, 2H,) 3.60-3.78 (m, 2H), 5.26 (t, 1H), 7.46 (d, 1H), 7.68-7.79 (m, 2H), 7.79-7.93 (m, 4H); MS: m/z 384.1 (MNa+).

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customdried
  5. customto afford 0.976 g of compound 747-D as a brown solid

Sources & evidence

ORD record
ord-a8274bae30aa4949afe4949d93bd1a82
Source dataset
uspto-grants-2014_08
Patent number
US08809327B2

Reaction notes

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