Chlorosulfonic acid → HCID 59347426, compound

HRID 42381Notes

Reaction equation

HRID 42381 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[Cl:6][C:7]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:8]=1[O:9][CH2:10][CH2:11][CH:12]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][C:13]1=[O:22]>>[Cl:6][C:7]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:8]=1[O:9][CH2:10][CH2:11][CH:12]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([S:2]([Cl:1])(=[O:5])=[O:3])[CH:19]=2)[NH:14][C:13]1=[O:22]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 59347425HCID 59347425, compound

Product 1

HCID 59347426HCID 59347426, compoundYield 47%

Conditions

Temperature
0 °C

Procedure

After cooling chlorosulfonic acid to 0° C. under N2, the 3-(2-(2,4-dichlorophenoxy)ethyl)-3,4-dihydroquinolin-2(1H)-one was added slowly and stirred at 0° C. for 1 h. The solution was heated to 50° C. for 10 minutes and cooled down to rt. After pouring the reaction mixture into ice, a white precipitate formed which was extracted with CH2Cl2. The organic layer was washed with H2O and brine, then dried over MgSO4 and concentrated in vacuo to complete dryness, giving the product as a white solid (2.4 g, 47% yield).

Workup

  1. temperatureThe solution was heated to 50° C. for 10 minutes
  2. temperaturecooled down to rt
  3. additionAfter pouring the reaction mixture into ice
  4. customa white precipitate formed which
  5. extractionwas extracted with CH2Cl2
  6. washThe organic layer was washed with H2O and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-25bd361ea928493589e7b5f69c7af2d2
Source dataset
uspto-grants-2013_09
Patent number
US08536195B2

Reaction notes

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