Chlorosulfonic acid → HCID 86655226, compound

HRID 1256158Notes

Reaction equation

HRID 1256158 reaction equation
Cl[S:2]([OH:5])(=[O:4])=[O:3].[F:6][C:7]([F:24])([F:23])[C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH2:18][S:19]([CH3:22])(=[O:21])=[O:20])[CH:12]=1)=[O:9]>>[CH3:22][S:19]([CH2:18][CH2:17][C:13]1[CH:12]=[C:11]([NH:10][C:8](=[O:9])[C:7]([F:23])([F:6])[F:24])[CH:16]=[CH:15][C:14]=1[S:2]([OH:5])(=[O:4])=[O:3])(=[O:20])=[O:21]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 86655224HCID 86655224, compound

Product 1

HCID 86655226HCID 86655226, compoundYield 43.1%

Procedure

Chlorosulfonic acid (5.8 g, 49 mmol) was cooled to 0° C., then 2,2,2-trifluoro-N-(3-(2-(methylsulfonyl)ethyl)phenyl)acetamide (2 g, 6.8 mmol) was added slowly. The reaction mixture was allowed to warm to room temperature. Two hours later, the reaction was poured onto ice. The aqueous layer was extracted with ethyl acetate 3 times. The combined organic phase was washed with brine, dried over sodium sulfate. The crude product was purified by pre-HPLC (column: Luna 300×50.0 mm, 10 um; liquid phase: [A-H2O+0.05% TFA; B-MeCN] B %: 0%-27%, 23 min) to give 2-(2-(methylsulfonyl)ethyl)-4-(2,2,2-trifluoroacetamido)benzenesulfonic acid (1.1 g, yield 28%).

Workup

  1. additionTwo hours later, the reaction was poured onto ice
  2. extractionThe aqueous layer was extracted with ethyl acetate 3 times
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customThe crude product was purified by pre-HPLC (column: Luna 300×50.0 mm, 10 um; liquid phase: [A-H2O+0.05% TFA; B-MeCN] B %: 0%-27%, 23 min)

Sources & evidence

ORD record
ord-0e5d4b8810a74f68882a018c96cde0c7
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

Loading…