Chlorosulfonic acid → 4-(2-Oxoimidazolidin-1-yl)benzene-1-sulfonyl chloride

HRID 746747Notes

Reaction equation

HRID 746747 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].C([N:13]1[CH2:17][CH2:16][N:15]([C:18]2[CH:23]=[CH:22][C:21](S(NC3C=CC=CC=3C(C3C=CC(F)=CN=3)=O)(=O)=O)=[CH:20][CH:19]=2)[C:14]1=[O:43])C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[O:43]=[C:14]1[NH:13][CH2:17][CH2:16][N:15]1[C:18]1[CH:23]=[CH:22][C:21]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 58664909HCID 58664909, compound

Product 1

HCID 214290354-(2-Oxoimidazolidin-1-yl)benzene-1-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To 1.5 mL (23.1 mmol) of chlorosulfonic acid in 3 mL of carbon tetrachloride at 0° C. was added slowly 500 mg (3.1 mmol) of the compound of Step 1. The reaction was almost completed after 2 h at 0° C. The reaction mixture was poured into ice water slowly, then filtered to collect the solids formed. The aqueous layer was extracted with chloroform (3×100 ml), and the combined organic layers were dried over sodium sulfate, filtered, concentrated in vacuo. The filtered solid and the crude material from the extraction were combined to provide the title compound (LC/MS found: 261.1)

Workup

  1. filtrationfiltered
  2. customto collect the solids
  3. customformed
  4. extractionThe aqueous layer was extracted with chloroform (3×100 ml)
  5. dry with materialthe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. extractionThe filtered solid and the crude material from the extraction

Sources & evidence

ORD record
ord-e4065a2568f149a8887165f4b43e54db
Source dataset
uspto-grants-2008_07
Patent number
US07393873B2

Reaction notes

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