Chlorosulfonic acid → 4-[(1,3-Dioxoisoindolin-2-yl)methyl]-1-benzenesulfonyl Chloride

HRID 1396061Notes

Reaction equation

HRID 1396061 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[CH:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:13]2[C:22](=[O:23])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:14]2=[O:15])=[CH:8][CH:7]=1>>[O:23]=[C:22]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:14](=[O:15])[N:13]1[CH2:12][C:9]1[CH:8]=[CH:7][C:6]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 75059Benzylphthalimide

Product 1

HCID 210844074-[(1,3-Dioxoisoindolin-2-yl)methyl]-1-benzenesulfonyl ChlorideYield 73%

Conditions

Temperature
60 °C

Procedure

Under N2 atmosphere, 11.26 mL chlorosulfonic acid was cooled in an ice bath, and under stirring 10.00 g n-benzylphthalimide was added portionwise over a period of 20 min. The ice bath was removed and the mixture was heated to 60° C. for 30 min. After cooling to room temperature, the mixture was cautiously poured into ice water and extracted twice with chloroform. The combined organic layers were dried over MgSO4 and concentrated to a small volume. The product was obtained by trituration of the concentrate with PA to give 10.44 g (73%) of a white powder. 1H NMR (400 MHz, CDCl3) δ 4.95 (s, 2H), 7.67 (d, J=8.43 Hz, 2H), 7.73-7.78 (m, 2H), 7.85-7.90 (m, 2H), 8.00 (d, J=8.43 Hz, 2H).

Workup

  1. additionwas added portionwise over a period of 20 min
  2. customThe ice bath was removed
  3. temperatureAfter cooling to room temperature
  4. additionthe mixture was cautiously poured into ice water
  5. extractionextracted twice with chloroform
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. concentrationconcentrated to a small volume
  8. customThe product was obtained by trituration of the
  9. concentrationconcentrate with PA

Sources & evidence

ORD record
ord-175035aa7e3a4ab6b2c7f0b18a490645
Source dataset
uspto-grants-2014_12
Patent number
US08901108B2

Reaction notes

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