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

HRID 1691564Notes

Reaction equation

HRID 1691564 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-471c2bdd00cc497d9349c7fccd01b179
Source dataset
uspto-grants-2012_04
Patent number
US08153682B2

Reaction notes

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